All 206 Strong Bad Emails from Homestar Runner, ranked

Over the course of 15 years, Mike and Matt Chapman, “The Brothers Chaps,” have created the most impressive body of work in the history of the Internet. Homestar Runner—a viral phenomenon that preceded YouTube, Facebook, Twitter, and Tumblr—is a website, a character, and a profoundly realized, self-contained universe. 

Originally drawn as a children’s book (mostly to prove to the world how easy it is to draw children’s books), Homestar Runner became a conduit for the Brothers Chaps’ silly, innocent, referential, satirical, loving humor. The site is full of all the colorful debris of American culture: discount electronics, text adventures, hip-hop tapes, glam metal, hot wings from the concession stand, and a town full of about 15 people who are all completely comfortable in their existence.

The most popular recurring feature of the site, familiar to any fan, are the Strong Bad Emails. Strong Bad sits down at one of his ancient computers, takes a question from a fan, and answers it in his usual aggro, 15-year-old-boy-as-Mexican-wrestler fashion. The Brothers Chaps have done 206 of these so far, and though updates to the site are more infrequent now, I don’t think they’re going to stop until they’re either dead or Flash finally caves in on itself. I take comfort knowing that no matter what, no matter how bad things get, Homestar Runner were always be there, ready to tell me about love, rock and roll, and breakfast cereal.

Congratulations, Homestar Runner, you’re in the hall of fame. To celebrate, we went ahead and ranked every single Strong Bad Email for your shock, perusal, and entertainment.

206) Brianrietta

The only cartoon in the entire Homestar hierarchy with a gay joke. Disappointing.

205) Lackey

Does a cantaloupe with a funny voice make you laugh? No? Maybe you should skip this one.

204) Tape Leg

OK, Tape Leg is a bad email, but I still kind of love it because its anti-humor became a long-running reference in the Homestar canon. I can’t help but respect it for that.

203) I She Be

If the idea of someone screwing up their grammar and typing “I she be” doesn’t make you laugh, then this email probably won’t make you laugh either.

202) Three Wishes

Kind of a nothing email. Strong Bad is asked what he’d do with the second of three wishes, and he asks for horns. There’s a heavy metal joke, and that’s about it.

201) Making Out

Some of these early Strong Bad Emails seem out of canon, or character. Like, the archetypical SB email is pretty simple: email song, read the email, cut-away to short cartoon about said email, back to Strong Bad on his computer. This one is just Strong Bad talking about how making out to Peter Frampton is stupid while promoting his hit single “You’re Really Ugly (But There’s No One Cute Around),” which, OK, not bad! But this is still like the prehistoric cave painting of Strong Bad emails.

200) Credit Card

There are much better emails, but I do enjoy Strong Bad stealing Homestar’s card information so he can buy multiple spaceships.

199) 12:00

Strong Bad recommends duct-taping an alarm clock to a VCR to solve the issue of blinking “12:00,” which is actually pretty sound advice, all things considered.

198) SB Email 22

The dawn of “screw all y’all.” Sure, it’s the shortest Strong Bad Email ever—but that debut still counts for something.

197) Spring Cleaning

Not much here, but it is the moment when the “Strong Bad deletes emails” trope went nuclear, and that means that this little cartoon is responsible for a great many memories that followed.

196) Lady…ing

The Brothers Chaps decided to do an email in the super, super old-school art style they used in the late ’90s. Which, fine? It just isn’t that funny.

195) Invisible

Strong Bad becomes invisible which, you know, is a fine premise for a Flash cartoon. Nothing really stands out except the sign-off, where he asks us to “eat your vitamins and pretend you’re hilarious” which is so, so on point.

194) Action Figure

Strong Bad’s action figure avatar dispenses radioactive goo and double-deuce action, but the real star is the homemade Peanut Strong Bad, which managed to have a pretty solid legacy in the Homestar canon.

193) Homestar Hair

A pretty slight entry about someone sending Strong Bad a picture of Homestar with hair. However, it gains some historical points for being the first cartoon where Strong Bad deletes an email.

192) Lures & Jigs

There’s not much here. It’s Strong Bad going fishing with Coach Z for 30 seconds. However, I do enjoy the public-access fishing show music they use.

191) Helium

Strong Bad inhales some helium. Fine, I guess.

190) Sugarbob

Not a great email, but I do find myself using the term “sugarbob” as a term of endearment all these years later. [Ed. note: Same. In fact, my wife won’t stop with it, ever.]

189) Narrator

Strong Bad narrates some of his friends’ everyday lives. I don’t know—it’s faces the same issue that many of the later emails have: A premise that sounds too much like a standup bit and not something that exists in the context of the Homestar universe.

188) Monster Truck

It’s Strong Bad doing a fake monster truck ad. “Awesome Cross ’98” is a great fake monster truck event name, but there’s not too much else.

Homestar Runner

187) Pizazz

The Brothers Chaps turn their satirical eye to network-television style event interviews, and it doesn’t totally click.

186) Technology

This isn’t awful, but Strong Bad making cell phone jokes feels like the most autopilot email ever.

185) Super Powers

Strong Bad shows us that he can focus his powers to pop off beer caps; moderate laughs ensue.

184) Guitar

It’s funny to think when I first watched this, I had no idea of the implications of holding up a lighter—or the BMW logo, for that matter!

183) Island

The best part of this email is the beginning, where Strong Bad gives a perfectly lackadaisical explanation of how getting stuck on a desert island usually works in cartoons. Everything else is average.

182) Disconnected

Someone writes in and asks Strong Bad what he’d do if his head was disconnected from his body, and the Brothers Chaps spend way too much time exploring the answer.

181) No Loafing

This is one of those “weird Strong Bad Emails” that doesn’t quite stick the landing. Maybe that’s just because jokes about motivational posters seem super clichéd now.

180) Your Friends

A cartoon I loved as a kid: Strong Bad performing a bunch of Looney Tunes slapstick on his friends. But as I’ve gotten older, I tend to prefer the more nuanced entries in the catalog.

179) Interview

Homsar was a character originally introduced in the second email ever, and now he gets an extended look in an email released nearly 50 entries later. Homestar Runner was always so good at eating its own tail.

178) Some Kinda Robot

The first Strong Bad Email is such a random, tossed-off thing. It’s about 40 seconds of Strong Bad yelling at some lady for implying that his head is a mask and not his actual face. Years later, Strong Bad Emails would be the de facto backbone of the Homestar Runner universe, but at the start they were just something to put out quickly in between larger cartoons. Yeah, it’s ranked low, and canonical first episodes do deserve the benefit of the doubt, but why focus on the inauspicious beginnings when there’s so much great content to get to?

177) Rampage

This one just kinda meanders around till it’s over, but it does have Coach Z laughing, so it really can’t be that bad.

176) Hygiene

The funniest thing about this email is that it comes from a fifth-grade boy; everything else is just OK.

175) Current Status

Bubs and Coach Z switching bodies is a gag worth the 30 seconds it’s given.

174) Mascot

I do love Used Electronics University.

173) 2 Years

We learn what Strong Badia will look like in two years. There’s a hole and a mural, and a couple of a giggles.

Homestar Runner

172) Being Mean

Towards the end of the primary SB email run you could tell that The Brothers Chaps were a little creatively spent on the many other projects they had going. Being Mean has a great premise, but it just doesn’t get there.

171) Fingers

Strong Bad attaches fake fingers to his boxing gloves because he’s tired of people asking him how he types, which is a recurring joke that requires quite a bit of context. Doesn’t matter, though, because the cartoon here is pretty average, save for Homestar’s fake arms.

170) Huttah

You know what? The Cheat might be the most overrated character in the history of Homestar. However, this email does prove just how popular he was in that 2003/2004 period. I’m pretty sure the Brothers Chaps built their house from Cheat merchandise sales.

169) Modeling

Strong Bad does some modeling, which is basically just an excuse to put Strong Bad in a polo shirt.

168) Love Poems

Strong Bad does a parody on Shakespearean sonnets, which isn’t exactly what I come to Strong Bad for.

167) Myths and Legends

Strong Bad tells us the origin of Strong Badia’s legendary bear-holding-a-shark legend—just another part of the fake nation’s history fleshed out.

166) Weird Dream

The only thing of note here is Strong Bad using the Cheat’s computer to answer an email. I’ve always loved how he used an eggshell iMac, which probably seemed super hip at the time.

165) Duck Pond

I still boot up the duck-feeding minigame when I’ve had a rough day.

164) New Hands

Strong Bad says he’d choose to get his hand replaced with a bucket, then realizes he’s an idiot, which is funnier than you might think!

163) Pop-Up

Someone writes in asking about a Strong Bad pop-up book, Strong Bad creates a pop-up book. Simple mathematics.

162) Bottom 10

Strong Bad gives his general “bottom 10,” which reads a little too much like a BuzzFeed list for my liking.

161) Marzipan

More logs on the longstanding “Strong Bad is the most overcompensating insecure weirdo in the universe” fire. I always thought Marzipan could’ve been a meaningful character with just a little more focus.

160) Garage Sale

“Coach Z, can I ask why you’re buying all the ‘great for babies’ items?’” “I’d prefer that you didn’t.”

159) Rated

I still barely know what this email is about, but it does have Coach Z and Bubs in it, so that’s pretty solid.

158) Cartoon

It’s a meta-joke about a cartoon character talking about himself in his own cartoon, which in the world of Homestar was bound to happen sooner or later.

157) Space Program

We learn about Strong Bad’s space program, which is a funny idea on paper, at least.

156) Time Capsule

Strong Bad puts some stuff in a time capsule, and things progress naturally from there. Points for the Stinko-Man appearance.

155) Stupid Stuff

Strong Bad gets outsmarted by Homestar, and it totally breaks his world. It’s a fantastic concept but could have been a little better.

154) I Love You

The debut of fhqwhgads, which would later be adapted into the best song that ever came out from Homestar Runner. That alone gets it up this list.

Homestar Runner

153) Portrait

It was only a matter of time that Strong Bad got emblazoned on black velvet.

152) Vacation

One of the more unique SB emails. Strong Bad goes on vacation and sends us postcards! Complete with narration! From what I understand, this was published around the same time the Brothers Chaps took their usual Christmas break—so good synergy, guys. It’s pretty funny, too!

151) Ghosts

A good Ghostbusters gag, a callback to a previous email, and a fantastic easter egg. This is, like, the most fundamentally sound Strong Bad email.

150) Strong Badathon

Olympics jokes. It could be worse!

149) Pet Show

The best part of this email is Strong Mad and Strong Bad rubbing glazed donuts on the Cheat’s fur to make it shine. Everything else is average.

148) Other Days

Strong Bad shows us what he does on the days he’s not checking his emails, and for whatever reason it doesn’t quite work.

147) Little Questions

The magic of the Brothers Chaps’ craftsmanship is the ability to nail super specific things with absolute perfection. In this case, what non-native English tends to sound like.

146) Anything

Homestar pours mountain dew all over Strong Bad’s computer, which, you know what? That’s still hilarious.

145) Autobiography

Strong Bad’s autobiography is full of lies and modest laughs.

144) Little Animal

The email that establishes Strong Mad and the Cheat’s odd-couple relationship as besties/part-time crooks, which is still one of my favorite tropes in the universe. Maybe not side-splitting, but still pretty cute.

143) Secret Identities

Strong Bad reveals his secret identities in the usual compendium format. Good Garth Brooks joke!

142) Bedtime Story

We learn about the Cheat’s bedtime routine, which is pretty boring until we venture to Moses Malone-land.

141) Cliffhangers

This email is a set-up to Strong Bad’s computer being kidnapped, which is good for the Homestar plot, but isn’t exactly hilarious outside of that.

140) Funny

Strong Bad embraces his most Bugs Bunny tendencies in an email aimed at the kids.

139) Halloweener

Certainly not an all-timer, but the “and finally, get your mom to make you a Strong Bad costume” kicker always makes me laugh.

138) Monument

The debut of the Thnikkaman, one of the most nonsensical ideas the Brothers Chaps ever had, but he plays.

137) Your Edge

Strong Bad and the Cheat “lose their edge” and try to regain it by stomping on casserole. Decent gags abound.

Homestar Runner

136) What I Want

A couple good lines on bad Christmas gifts, but this feels too much like a stand-up bit for my taste.

135) Trevor the Vampire

I’m still mourning the death of Trevor.

134) The Facts

Kind of a random cartoon where we get a thorough evaluation on what makes Strong Mad tick. I thoroughly enjoy the Doug the Dino claymation.

133) Imagination

We meet Strong Sad’s imaginary friend, but easily the best part is pubescent, acne-covered Strong Mad shouting, “GIRLS ARE CONFUSING.”

132) Candy Product

Strong Bad invents his own candy bar, and I have to give it up to the commercial song for featuring the line “Y2K turned out all right!”

131) Looking Old

Strong Bad holds a marketing meeting to figure out how to appeal to young people who eat their yogurt from a tube. My favorite part is Marzipan’s HGTV reimagining of Strong Bad’s face.

130) Depressio

This might be the bleakest Strong Bad Email. Someone asks Strong Bad to tell Strong Sad he sucks, so he does. There’s really not much of a joke, and that makes it kind of fabulous. It’s funny because it pins the cruelty on the viewer—like, “hey, now Strong Sad is upset because you told us to do this to him, happy?” Way more insight than your average Flash cartoon.

129) Rough Copy

This cartoon ends with Strong Bad and the Cheat covered in barbed wire and starring in a cop drama, so that’s pretty good.

128) Dictionary

Strong Bad’s dictionary is necessary but also not entirely excellent.

127) Caffeine

Tweaker Strong Sad is so good. They really should’ve done more with him.

126) Lady Fan

Workout Homestar is pretty solid, and I’m a big fan of the scoreboard showing negative numbers as Strong Bad fails to do pushups.

125) Extra Plug

Strong Bad gets a pair of light-up electric boots that he’s very excited to wear to Club Technochocolate. Along the way he inadvertently kills the power in his own house. I love this email for its supremely random gags, like Homestar bringing a bottle of Mountain Dew in a popcorn bucket and Andy Griffith’s head taped to the TV.

124) Diorama

Strong Bad makes a diorama, summoning very fond memories of every shoebox project we’ve ever put together.

123) Property of Ones

Earns some points for being the first major artifact in the “cold ones” motif. “A one that is not cold is scarcely a one at all” is a wise comment indeed.

122) Hremail3184

Strong Bad comes out of email retirement and blows up the Lappy. It’s funny becuase there’ve only been like five cartoons since (2008/2009 was a dark time for Homestar Runner).

121) Magic Trick

Strong Bad takes a few minutes to make fun of all the different flavors of magicians to impress a Swedish girl. The David Blaine burn stands out.

120) Theme Song

A couple of good fake Strong Bad Email theme songs, which is a totally understandable premise for a Strong Bad Email.

119) Original

The Brothers Chaps use a lifelong history of watching old sitcoms to invent a scenario where the “original Bubs” has to be replaced in a number of hackneyed scenarios. Kinda clever and kinda funny!

118) Pizza Joint

This is basically a tribute to Habbo Hotel and other weird early-2000s 3D chatrooms, so I can’t help but love it.

117) Unnatural

They turn Bubs into Godzilla, because why not.

116) Origins

It’s funny how many Strong Bad Emails focus on the history and context of random minutiae in the Homestar universe. We learn how the Stick, a geographic landmark, gained its notoriety.

115) Business Trip

“The Cheat got promoted to Junior Executive of Not Having to Go On Pointless Business Trips!”

114) Bike Thief

I’m strongly in favor of Strong Bad using the “ponytailed Feed-the-Children guy on college campus” tactic to steal a bike.

113) Crying

Strong Bad draws a one-legged dog named Lil’ Brudder who’s determined to “make it on his own,” and Homestar has a complete mental breakdown. Stands as an important prototype of stuff like Clickhole.

112) Shapeshifter

Strong Bad shapeshifts into some stuff and makes fun of the Wonder Twins. Pretty standard.

111) License

Strong Bad makes some jokes about unlicensed cash-grabs, including animated movies like “Jungle Animals in Decidedly Non-Jungle Situations.”

110) Record Book

The beautiful thing about Homestar Runner is that both poop jokes and Paradise Lost references can exist in the same cartoon.

109) Coloring

Any email that lets you download a Limozeen coloring book is fine by me.

108) Yes, Wrestling

I’m a wrestling fan, so obviously I’m predisposed to like this, but I really feel like Il Cartographer could’ve gotten over in real life.

107) Trading Cards

A good Magic joke, a good Pokémon joke, and a good Garbage Pail Kids joke in a loving send-up of trading card madness.

106) Theme Park

Strong Bad was always going to invent a theme park.

105) Children’s Book

When Strong Bad writes a children’s book, he teaches the kids important words—like “linebacker.”

104) CGNU

A lot of great stuff here. It’s the first deep dive into Crazy Go Nuts University, one of Strong Bad’s many projects, and we learn that the application for this prestigious institution requires an “art test”—literally just drawing a guy with a big knife. Note that you can get your degree in “cheesing people off” or “total spaceship guy.”

Homestar Runner

103) Retirement

A nice little throwback where Strong Bad’s two other older computers hold the Lappy hostage.

102) Lunch Special

I like how this email goes off the deep end immediately. Like, Strong Bad creates this mythology in the first few seconds where if you get Bubs to say “Sbu” he has to give out free lunch specials. Why? Don’t worry about it, just enjoy the cartoon.

101) The Movies

I’ve always loved how the Brothers Chaps identified the perfect things to ridicule—in this case, the movie theater trivia slides that come before the previews.

100) Slumber Party

The definitive guide to having fun at a slumber party includes the phrase “Unpopular kids’ dads definitely still play video games.”

99) Buried

I like that the Taranchula metal detector plays a guitar solo when it goes off.

98) Replacement

Strong Bad screens the members of the Homestar cast to see who will replace him after he retires. Inessential but funny.

97) Secret Recipes

Nothing is this email matters outside of Coach Z staring at a basketball and saying “Man, what is this thing? A bounce thing?”

96) Underlings

Strong Sad doing a connect-the-dots puzzle that says “WE’RE GONNA NEED YOU TO FLUSH TWICE” is a pantheon-level Homestar Runner moment as far as I’m concerned.

95) Dreamail

Strong Bad imagines what his dream email would be, which is a decent gag. The best part is how said “dreamail” is sent by “128 hot Katies.”

94) Videography

As someone who spent a lot of time growing up watching my grandpa’s home movies, this speaks to me.

93) Your Funeral

Strong Bad’s hypothetical funeral is about as metal as you think.

92) Nightlife

I’m a huge proponent of Club Technochocolate, and Strong Mad’s bouncer bit—where he makes his first real joke as a Homestar cast member—is more than worthwhile.

91) Hiding

The Homestar cast play hide and seek, and, as usual, have way more fun than we ever would.

90) Colonization

A decent email about how Strong Badia was colonized. Love that Strong Bad was driven from his homeland for putting ketchup on eggs.

89) Pom Pom

Pom Pom is such an underrated character; I was always bummed that he didn’t get the shine he deserved.

88) Caper

As far as chintzy Casio Homestar bangers go, “The Cheat is Not Dead” is probably in the top three.

87) Couch Patch

We learn the history of the patch on the couch in Strong Bad’s basement, which is very specific and not as interesting as it probably should be.

86) Environment

God, that image of Coach Z cooking his hot dog by holding it under a hot shower just kills me every time.

85) Theme Party

When I was a kid, the idea of throwing a “frat party”-themed party went way over my head. Now it’s amazing.

84) Mile

I’ve always really enjoyed the Cheat’s fake, in-universe Flash cartoons, and this is the first time they’re given a major stage.

83) From Work

I like how The Brothers Chaps never really fleshed out why Strong Bad would occasionally wear a company polo shirt at an office, but it always lead to some memorable cartoons.

82) Boring (Really)

In which, for the first time in Homestar history, nothing really happens. Not particularly funny, but a good subversion!

Homestar Runner

81) More Armies

I never thought Homestar Runner would parody something as unfunny as a military job fair, but they nail it here!

80) Sisters

In retrospect, the implications that Strong Bad would happily fuck a groupie and her sister is rather strange, but this was still one of my favorite emails growing up, and it holds up.

79) Fan Club

In which we learn about the existence of the Deleteheads, Strong Bad’s own in-universe fan club. It’s so good.

78) Road Trip

The bit where Strong Bad says that every road trip needs a good inside joke, and that these days he makes up the inside joke ahead of time, is one of the best observations in the Homestar legacy.

77) Part-Time Job

We learn that Strong Bad’s part-time job involves him standing outside of Bub’s Concession Stand dressed like a hot dog with a sad clown face. That’s pretty freakin’ strong.

Homestar Runner

76) Impression

This became the formula for a number of Homestar Runner cartoons. A “let’s have a tournament to see who has the best Strong Sad impression!” type setup, with each member of the cast taking their shot. It works, but it’s not super memorable.

75) Four Branches

A bunch of really good Homestar bits, including him somehow getting stuck in a water cooler.

74) Specially Marked

Strong Bad talks about how some cereals are made of things that grow in Iowa, like corn, wheat, oats, and fundamentally sound basketball players.

73) Keep Cool

The Homestar cast enjoys a wonderful afternoon at the pool! Who could possibly say no?

72) Army

General Homestar is so great. DO YOU HAS THE FIVE BUCKS!

71) Sbemail206

From the ashes, Strong Bad Emails emerged after a five-year hiatus to take down the bullshit rise of Internet April Fools’ Day, complete with a great Kickstarter joke. Come back soon, Strong Bad, we need you.

70) Chair

“Do you have anything less anthrax-y” “I’ve got this old Winger album!” “Well, you’re right, that is less Anthrax-y!”

69) Big White Face

Hey look! A Poopsmith-centric email!

68) Web Comics

In 2015, long past the heyday of webcomics, this email might seem kinda dumb and silly. In the middle of that zeitgeist, this was gold.

67) Unused Emails

The best email deletion in the history of Homestar Runner.

66) Superhero Name

Here we meet Strong Badman in an email that really isn’t much on its own. However, it is the first alternate-universe version of a Homestar Character we meet, which becomes a consistent theme going forward.

65) The Bet

“Here’s my 200 pound bag of au gratin potatoes—it’s an ’83!”

64) Labor Day

I still say “Labor Dabor” every Labor Day.

63) The Process

Strong Bad shows us the “process” of answering an email, which is literally something we see every week anyway. It’s the most meta Strong Bad email, and that makes me happy.

Homestar Runner

62) Car

In which Strong Bad gets an email about his car and immediately veers way from the topic to the point where Homestar is showing off the hydraulics on his propellor cap.

61) Redesign

A send-up of modern graphic design, thanks to the Cheat!

60) Personal Favorites

When I watched this as a kid, I had no idea that all the emails mentioned in this were fictional—and seriously spent hours scouring the website to find them.

59) Winter Pool

Toward the end of their run, the Brothers Chaps were making Strong Bad Emails that could totally work as saturday morning cartoons. They seriously never fell off, especially when they’re working with a pool full of red Jell-O.

58) Independent

In the months before Homestar would go on a five-year long hiatus, I’m glad the Chaps made some time to make fun of 500 Days of Summer.

57) Cheatday

The Cheat answers a few emails by simply typing “yeah man, I’ll gnaw your face off,” which is a good enough gag to get this in the top half.

56) Death Metal

We finally put a face to Taranchula! Strong Bad’s evaluation on how death metal pastiche works is spot-on and hysterical.

55) For Kids

That “Stave it Off” song is still the funniest thing ever for some reason.

54) Senior Prom

A really good, really loving parody of all prom-related fiction. I like it when the Homestar cast aren’t comedians, just people inhabiting their weird little world.

53) 2 Emails

Strong Bad being unable to get laid is a surprisingly enduring theme.

52) ISP

Homestar reading the tech support script without changing any of the pronouns = underrated email.

51) Homsar

This is the second Strong Bad Email, which means it’s about 40 seconds long. But it does mark the debut of Homsar, one of my favorite characters. I like how Homsar canonically died in his first moment onscreen and still shows up to this day.

50) I Rule

Wanna know why Homestar Runner has persisted? It’s because when Strong Bad shows us his kingdom, it’s an abandoned patch of dirt with a loose tire leaning against a white fence, and there’s a sign that reads “Population: Tire.” That’s so pitch-perfect that it almost makes me angry.

49) High School

The Homestar cast in high school, middle school, and other eras, which you know you want to see.

48) Old Comics

This has always been one of my favorites because the Brothers Chaps are able to identify exactly what makes old-guard comic strips so egregiously unfunny.

47) Local News

The Brothers Chaps are masters at parodying the hazy memories of low-budget TV, so naturally the Strong Badia local news hits the mark exactly.

46) Sibbie

And I’ll never ever ever ever ever ever write a song about a Sibbie. More default Casio magic from the Cheat and Strong Bad.

45) Animal

The first email on the Lappy! And a romp through a bunch of weird Flash-gradient vomit. Pray for the Huuuuuuuuuudge.

44) English

Strong Bad’s fake English paper is too real, especially when he triple-spaces it.

43) Date

“OK, let’s do it again, what do you think I’m going to say next? Sid Hoffman or Sid Frenchman?” “This is the dumbest game I’ve ever played.”

42) Do Over

A lot of quality content here. Homestar dressed as the Cheat for some reason, callbacks to ancient emails, and a nice fulfilling arc at the end!

41) One Step Ahead

An underrated email. It’s basically a simple choose-your-own adventure game and works as a quasi-prototype for the peak Homestar years, when Strong Bad Emails were long, complicated weekly shows. I still play that minigame where you throw dodgeballs at Strong Sad sometimes.

40) Different Town

Another underrated email that features probably the best song in the history of the site. The ballad of the Modestly Hot Girl still gets me.

39) Morning Routine

Sometimes Strong Bad Emails would be very weird and very nonsensical—which is to say they’d dedicate an entire plot to Strong Sad digging eggs out of the living room couch while Strong Bad tries to answer a question. This is probably the best example of that type of absurdity.

38) Haircut

Strong Bad comes up with some new eyebrows for Strong Mad, including “a dog and also a cat shaped eyebrows.” Wonderful.

37) Suntan

Can’t argue with Strong Bad drawing Sharpie-abs onto his belly and the phrase “I could be a thousand-aire.”

36) Rock Opera

Strong Bad takes one word from each of his previous 125 emails and turns it into a rock opera, and it’s actually beautiful.

35) The Show

Strong Bad gets an email asking why Homestar doesn’t do anything funny anymore, which prompts the Brothers Chaps to deliver a very Homestar-centric cartoon. Much needed!

34) Email Thunder

The perfect 200th episode. A bunch of good callbacks, plus a decent plot twist that turns the entire series on its head. If this ends up being the last super-relevant Strong Bad Email, they went out with a bang.

33) Studying

Sometimes all you need to do to demonstrate why a Strong Bad Email is top-tier is with a single quote: “Why do you think she’s calling you? I mean, you’ve got the potential here to get first, second, and quite possibly even third base. So unless you’re studying a book called This Book is Better Than First, Second, and Quite Possibly Even Third Base, I suggest you hightail it over to your girlfriend’s house ASAP, man!”

32) Flag Day

In which we learn Strong Badia’s flag is a snake in a tire with its tail curled around a knife. We also get the Strong Badia National Anthem, where the “ones are always cold.” So yeah, you can’t really put this anywhere else but the top quarter overall.

Homestar Runner

31) Privileges

One of the special things about Homestar Runner is its willingness to introduce weird new elements to its world on a weekly basis. The Cheat’s “privileges reward card” is a striking example.

30) Gimmicks

This is a first for so many reasons. The actual content of the email is someone calling out Strong Bad for using “gimmicks” in his responses, as opposed to the old-school entries where he’d just talk for a while. It also marks the first death of the Tandy 400. The cycle of Strong Bad’s computers always served as an unofficial way to keep track of Homestar Runner’s various eras, which makes this ground zero for that tradition. It’s also a funny, meta cartoon—exactly the way I like my SB emails.

29) The Paper

I’m not sure why The Brothers Chaps decided to kill off the Paper, but I guess Strong Bad had to upgrade to a color printer sooner or later. This is funny and surprisingly heartfelt for an inanimate object that didn’t get much character development at all.

28) Long Pants

One of the weirdest and most delightful Strong Bad Emails ever. Homestar goes insane in daisy dukes, which is something I didn’t know I needed.

27) Geddup Noise

Goddamn, I adore this email. A Fugazi joke, Club Technochocolate, the weird and surprisingly thorough examination of an aspect of the Homestar universe that nobody would ever expect or ask for. This is the Brothers Chaps at their absolute best.

26) Radio

Strong Bad’s fake college radio broadcast is still one of the funniest things on the site.

25) Cheat Talk

This one is really good in a way I can’t explain. The Brothers Chaps are able to make the word “Douglas” funny. We don’t deserve them.

24) Dullard

Homestar plays such a great airhead tech-bro. His soliloquy on his workout still makes me fall out of my chair.

23) Montage

Strong Bad falls in love with a wagon full of pancakes, which is just the best. I’m obsessed.

22) Crazy Cartoon

The debut of Sweet Cuppin Cakes! In later years, the Brothers Chaps would flesh this alternate universe out, but this is a stellar origin story.

21) Butt IQ

This is a cartoon about the Transitive Property of Butts, and I am but a simple man with simple tastes.

20) Alternate Universe

A big celebration of all the different versions of Strong Bad that have popped up over the years—the ideal way to celebrate the 150th email.

19) Stand-Up

We get to witness tiny Strong Bad’s disastrous talent show stand-up set. The Brothers Chaps never overdid it, and that’s what makes them geniuses.

18) The Bird

The dawn of the double-deuce, which is still one of the finest things the Homestar universe ever produced. Also Strong Bad’s downtrodden “OK, until next week. Send me an email, and I will more than likely flip you off” is a top-tier signoff.

17) 50 Emails

One of my favorites of all time. Part of the problem with the Strong Bad Emails becoming such a dominant feature on the site was that a lot of the tertiary characters got squeezed out. Here we had Homestar and Strong Bad onscreen together being very funny. That’s all I really ask for.

16) Mini-Golf

The best Sweet Cuppin Cakes bit ever, and that’s saying something.

15) Dragon

A stone-cold classic simply for the first appearance of the mute, beefy-armed dragon Trogdor, who’s still somehow the most iconic character in the series all these years later. The cartoon itself is good, “Trogdor was a man, he was a dragon-man, actually he was just a dragon, but he was still TROGDORRRR” is an all-timer, but this is still mostly relevant for historical purposes.

Homestar Runner

14) The Basics

This is an email I didn’t get at all as a kid but have come to adore as an adult. Strong Bad is asked to teach the emailer the “basics,” and he kinda stumbles and recommends some schoolyard bullshit like telling someone to look the other way and pouring soda down their shirt. It’s the first inkling of my all-time favorite Homestar trope, that Strong Bad is a total poser who’s deeply insecure about everything. It’s the sort of long-term character development that has literally never existed anywhere else in Flash cartoons.

13) Kind Of Cool

In which we meet Senor Cardgage, the creepy, semi-homeless, combover version of Strong Bad, eating melted candy bars and selling used stereos. One of the very best characters to come from a Strong Bad Email.

12) Band Names

Strong Bad is asked to come up with some band names, and he promptly comes up with some of the best band names you’ll ever hear. “LIMOZEEN” and “TARANCHULA” went on to become longtime recurring jokes, but there’s also some incredible nuggets (Z’Nuff) buried in there, too.

11) Best Thing

We get the Limozeen Saturday Morning Cartoon Show, which is one of the best tangents The Brothers Chaps ever went down.

10) Website

The definitive document on crappy early 2000s webpage design. We need to save this one for the aliens.

9) Dangeresque 3

Strong Bad returns to the well to gives the desperate world more Dangeresque. Nothing will ever reach the heights of the original, but this is still easily one of the best emails.

8) Techno

In which Strong Bad combines four low-bit noises into the most defining song in Homestar history. The introduction of the term “lightswitch rave” only solidifies this as a crucial moment.

7) Virus

The Compy 386 gets a wrecked by viruses, and the very nature of reality starts to fall apart. Truly one of the finest reality-bending freakouts in the history of Flash.

6) Japanese Cartoon

Strong Bad nails a Dragonball Z parody better than any of us ever could. Stinko Man—the Japanimation version of Homestar Runner—would spin off into its own universe, which proves the Brothers Chaps always knew when their ideas were gold.

5) Flashback

Email 100! This was hotly anticipated when it first arrived, and it brought a perfect mix of humor and nostalgia, which is why I go to Homestar Runner to this day.

4) Stunt Double

The dawn of Dangeresque, the most important alternate universe in Homestar Runner. It makes perfect sense that the Brothers Chaps would nail silly action movie tropes.

3) Concert

Obviously I’m some random indie rock nerd, so I’m biased, but the Brothers Chaps’ deep investigation into what separates Limozeen from their Pavement stand-in Sloshy is definitive brilliance. Also, Sloshy is a profoundly believable name for a jangly ’90s Matador band.

2) Video Games

The Brothers Chaps’ craftsmanship was so far beyond any of their peers it’s actually kind of ridiculous. Not only do they create a lengthy email with multiple art styles depicting multiple video games, they then program those games in Flash to be played at the end of the email. Seriously, these guys put stuff like this out on a weekly basis, and I truly do miss their dedication.

1) Comic

The origin of Teen Girl Squad, still my (and most people’s) favorite idea in the history of Homestar Runner. Cheerleader, So-And-So, What’s-Her-Face, The Ugly One. Number one with a bullet. 

Homestar Runner

Photo via Homestar Runner

Luke Winkie

Luke Winkie

Entertainment and sports reporter Luke Winkie has written everywhere from A.V Club to Vice, including Sports Illustrated, Rolling Stone, Kotaku, Playboy, Mel, and Polygon.