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Illustration via Max Fleishman

A timeline of the Lonely Island’s trail-blazing Internet comedy

From to 'Popstar.'


Chris Osterndorf


Posted on Jun 3, 2016   Updated on May 26, 2021, 4:21 pm CDT

Made up of Andy Samberg, Akiva Schaffer, and Jorma Taccone, the Lonely Island has had a singular career in Hollywood, and more importantly, online. Before Saturday Night Live, during, and after, the Lonely Island’s goofy sketches and music videos embodied a DIY, viral-ready sensibility which would go on to define the current climate of viral humor. 

Now, on the eve of Popstar: Never Stop Never Stopping, the group’s breakthrough motion picture, it’s time to take a look back at everything they’ve given us over the years. Here’s how Samberg and friends went from obscure Internet sketch group to Hollywood comedy superstars.

1990 (approximately): They all meet

Schaffer and Taccone connected with the one-year-younger Samberg while attending middle school in Berkeley, California.

2000: The Lonely Island is born

Ten years later, they graduate college and decide to move to Los Angeles and start making videos together. The group and their website’s namesake were born out of an apartment building they lived in which was cut off from the world by traffic.

September 2001: ‘Ka-Blammo!’ is released

Uploading to such platforms as iFilm, Atom Films, and at the time, the Lonely Island’s first notable video, “Ka-Blammo!”, hits the Internet. The group released the video under the name Incredibad, which would eventually become the title of their first album. The clip’s joke-rapping style would serve as a preview to much of their later work. Today, “Ka-Blammo!” has over 1.7 million views on YouTube.

December 2001: The group produces their first pilot

The trio got representation off their first TV pilot for a show which they named after themselves.The title of said pilot was called “White Power!” and finds the guys getting addicted to teeth-whitening. In a sign of the times, their agents asked if they could convert their videos to VHS tape, since none of them had high-speed Internet. “White Power!” is notable, among other reasons, for including an over-enthusiastic Kiefer Sutherland trying to break up a mugging.

February 2003: The group’s second pilot arrives

The Lonely Island’s second pilot, Regarding Andy, sold to Comedy Central, although the network ultimately didn’t do anything with it.

March 2003: The Lonely Island meets Dan Harmon

In 2003, the group began calling themselves “the Dudes” and contributing to Super Midnight Movie Club, Dan Harmon and Rob Schrab’s precursor to the revolutionary website Channel 101, which served as one of the first hubs for comedy videos on the Internet. It was there that they released “Nintendo Cartoon Hour,” in which the guys talked over old Nintendo games. Today, it looks pretty simple, but in age before PewDiePie, you can see why gamers and comedy nerds alike would’ve eaten it up.

July 2003/August 2003: The group’s relationship with Channel 101 continues

The Lonely Island released two episodes of a show called Ignition TV Buzz Countdown on Channel 101 in July and August of 2003. Per Channel 101’s format, the audience voted to keep the show around for a second episode after the first was released, but did not elect to bring it back for a third. The show was a parody of MTV’s Total Request Live, with some pretty NSFW content thrown in for good measure.

October 2003-April 2005: Welcome to ‘the Bu’

A parody of Fox’s The O.C., The Bu (as in Malibu) was a video series from the Lonely Island which co-starred Scrubs’s Sarah Chalke and ran for eight episodes from 2003 to 2005. Although it was one of the first projects to really put the guys on the map, they actually abandoned it and let other Channel 101 talent take it over for its last few episodes, while they were busy developing a pilot for Fox (we’ll get to that). “The Bu” remains one of Channel 101’s most popular shows ever, and the Lonely Island would later reference The O.C. on SNL in the digital short “The Shooting.”

June 2004: The Lonely Island takes a trip to ‘Football Town’

The Dudes created “Football Town” for a 2004 pilot that Channel 101 pitched to FX, which was set to be co-hosted by Jack Black. The pilot never got picked up however, and Channel 101 wouldn’t get another show on the air until VH1 aired 2007’s Acceptable TV.

September 2003: The Lonely Island introduces us to ‘Just 2 Guyz’

One of its most popular non-SNL clips ever, “Just 2 Guyz” is perhaps the Lonely Island’s best low-budget rap song. Akiva and Jorma plan and hang out at a terrible party, and talk shit about their friend Steve (Samberg). Today, “Just 2 Guyz” has been viewed over 10 million times, and a sequel, “We Like Sportz” was released in 2008 and appeared on Incredibad.

March 2005: Jorma shows everybody ‘My Pants

Another early Lonely Island classic, legend has it that Taccone asked Schaffer to shoot this video as his birthday present.

May 2005: ‘The Dudes’ get left behind for Awesometown

Awesometown was a 2005 pilot the Lonely Island did for Fox, later released in multiple versions on the group’s website. Made for just $70,000, the live sketch show isn’t bad, but it doesn’t quite utilize the guys’ talents in the best way. There’s a reason they made their name not on live sketches, but on the digital shorts which served as SNL interludes. Schaffer later elaborated on this, saying, “When we tried to explain why our stuff would be different, we’d say that most sketch shows came from the stage, from Second City or wherever… Our comedy comes from the medium of TV and music videos. A lot of our jokes are editing- and music-based.” This was, of course, what would also make The Lonely Island’s comedy so perfect for the digital age.

June 2005: The Lonely Island meets Jimmy Fallon

While serving as writers for the 2005 MTV Video Music Awards, the Lonely Island impressed host Jimmy Fallon. This helped lead to…

October 2005: The Lonely Island debuts on SNL

It’s easy to forget now, but when they were hired in 2005, the Lonely Island were basically the first group of comedians to make the transition from the Internet to SNL. People at the show had already seen their work, and pretty soon the guys got the attention of Lorne Michaels and Tina Fey, who hired Schaffer and Taccone as writers and Samberg as a cast member.  

November/December 2005: ‘Bing Bong Brothers’ and ‘Lettuce Heads’ help the guys find their way

There was a grace period, however. When Schaffer and Taccone struggled to get sketches on the air, they released “Bing Bong Brothers,” a parody of Ying Yang Twins’ “Wait (The Whisper Song).” After being widely shared on the Internet, the clip was eventually picked up by G4’s Attack of the Show. “Bing Bong Brothers” paved the way for “Lettuce,” SNL’s first digital short from the Lonely Island. Although it was initially cut after a dress rehearsal in November, “Lettuce,” an irreverent short which features Samberg and Will Forte talking about grief over heads of lettuce, helped to pave the way for the guys’ future on SNL.

Dec. 17, 2005: ‘Lazy Sunday’

It’s hard to overstate the effect “Lazy Sunday” had on the Internet’s relationship to comedy. Featuring Samberg and fellow castmember Chris Parnell walking around New York rapping about cupcakes and The Chronicles of Narnia, it wasn’t immediately evident that the sketch would become a classic. The effect of “Lazy Sunday” wasn’t fully felt until a week later, when it had amassed 2 million views on YouTube, becoming the first SNL sketch to ever truly go viral. It even forced the network to put its sketches on iTunes (a revolutionary move at the time.) Moreover, it set a precedent for late night and sketch shows which still stands today: Whether your ratings are good or not, you can stay relevant by getting millions of views online. As Taccone later told Variety:

When “Lazy Sunday” came out, we were watching numbers on a site we had never heard of. It was this double whammy: we always got associated with the Internet, but it was television that made it possible. Then it became the currency of the popularity of our shows – oh, this one is really popular because it had X hits. YouTube really changed that, honestly. There was this second life to television.

NBC eventually took “Lazy Sunday” off YouTube, in an indication of the ongoing battle networks would wage in the coming years to control content. But by the time that happened, “Lazy Sunday” made its mark, and both YouTube and SNL were forever changed.

March 2006: Natalie gets nasty

How do you follow up one giant, game-changing video? With Natalie Portman, that’s how. In March 2006, SNL released “Natalie’s Rap,” which featured Portman taking part in all kinds of foul situations. The format of enlisting a celebrity to play with their image became a classic Lonely Island trick, which they would employ throughout the rest of their career on SNL, and which remains a staple on Jimmy Kimmel Live! and The Tonight Show with Jimmy Fallon.

December 2006: Time to put your you-know-what in a box

The group’s next viral hit found Justin Timberlake perfecting the technique mentioned above, in one of his most memorable appearances on SNL. “Dick In a Box” spawned two sequels featuring Samberg and Timberlake’s ‘90s R&B characters, with 2009’s “Motherlover” and 2011’s “3-Way (The Golden Rule).” The song also won an Emmy and made waves when an uncensored version appeared on YouTube.

Aug. 3, 2007: Hot Rod fails to pick up steam

The first film that the three Lonely Island members worked on together, 2007’s Hot Rod was directed by Schaffer and featured Samberg and Taccone in the cast. It bombed at the box office, though some have since declared it an innovative cult classic.

Feb. 3, 2009: The Lonely Island takes us on a boat

As Vulture’s Jesse David Fox points out, “Samberg, Shaffer, and Taccone have always been determined to make their jokes amount to more than the fact that they’re three white guys making rap.” This is why no song is probably as emblematic of what the Lonely Island does so well as “I’m on a Boat.” Featuring a hook by T-Pain and a “Big Pimpin“-style video to accompany it, “I’m on a Boat” looks and feels so much like an actual rap song that if you weren’t paying attention you’d probably miss how funny it is. The production is great, Samberg and Schaffer bust out their best flows, and you can listen to the song as a comedy fan or a rap fan. Proving its power to transcend, “I’m on a Boat” eventually went platinum and was nominated for a Grammy.

Feb. 10, 2009: Incredibad finally arrives

The Lonely Island’s first studio album, featuring material that had been and would be featured on SNL, became the No. 8 best-selling rap album of 2009.

2010: Jorma quits SNL

He continues to work on shorts with Andy and Akiva, as well as directing a film.

May 21, 2010: MacGruber hits theaters

Taken from a series of MacGyver parodies which aired over several years on SNL, MacGruber is Taccone’s first feature film as a director and includes SNL mainstays Forte and Kristen Wiig in the cast. Unfortunately for Taccone, it’s another box-office bomb.

December 2010: ‘I Just Had Sex (feat. Akon)‘ premieres on SNL

The video goes on to become the Lonely Island’s most popular video on YouTube ever, with over 250 million views.

May 10, 2011: The group’s second album is released

Turtleneck & Chain featured many of the group’s continuing hits on SNL and earned a Grammy nomination for best comedy album.

May 12, 2012: The Lonely Island releases its 100th digital short

The video features cameos from and references to much of the other work. A week later, Schaffer and Samberg tape their last show for SNL.

June 15, 2012: Andy Samberg stars with Adam Sandler in That’s My Boy

It appears that audiences were not ready to see the stars of two SNL generations come together, as That’s My Boy went down as the third bomb in the Lonely Island crew’s cinematic career.

July 27, 2012: The Watch hits theaters

The next movie from a member of the Lonely Island starred Ben Stiller, Vince Vaughn, Jonah Hill, and Richard Ayoade with Schaffer returning to the director’s chair. In keeping with tradition, The Watch was critically savaged and also performed horribly at the box office.

Jan. 25, 2013: The Lonely Island returns to SNL with ‘YOLO (feat. Adam Levine and Kendrick Lamar)’

Depicting the guys’ freaking out about the future and every hint of danger that comes with it, “YOLO” also featured inspired turns from both Lamar and Levine.

May 7, 2013: ‘Spring Break Anthem’ debuts on Funny or Die

Premiering the clip on Zach GalifianakisBetween Two Ferns, “Spring Break Anthem” included appearances by James Franco, Edward Norton, and Galifianakis himself, in what was half a sendup of the film Spring Breakers and half an endorsement of same-sex marriage. It was around the same time that the Lonely Island unveiled “Wack Wednesdays,” where the band would release a new song and video each week (a premise clearly taken from Kanye West’s GOOD Fridays series in 2010).

June 7, 2013 The Lonely Island releases The Wack Album

The album featured songs including “3-Way (The Golden Rule),” “YOLO,” and “Spring Break Anthem.”

September 2013: Kyle Mooney and Beck Bennett are hired on SNL

OK, this one doesn’t have to do with the Lonely Island directly. Still, it’s hard to imagine Mooney and Bennett, who made their names on YouTube with their Good Neighbor sketch group, getting hired if not for the path the Lonely Island set out for them. Mooney has even taken to doing digital shorts like the Lonely Island often did, although his are usually far weirder than anything his predecessors came up with.

February 2014: The Lego Movie teaches us that ‘Everything Is Awesome’

The release of The Lego Movie in 2014 also heralded the release of its ridiculously infectious theme song, “Everything Is Awesome,” a collaboration between the Lonely Island and Tegan and Sara. The tune would go on to earn an Oscar nomination for best original song.

August 2014: It’s announced that the Lonely Island will be getting a standalone movie

Little is known initially other than that it will be set in the music world and Judd Apatow will also be working on it.

March 2016: The trailer for Popstar: Never Stop Never Stopping is released

The clip introduces us to Samberg’s Conner4Real, the Bieber-esque pop star of the movie’s title. Singles from the movie including “I’m So Humble,” “Mona Lisa,” and “Finest Girl,” the last of which premiered on SNL, soon follow.

May 16, 2016: The Lonely Island drops by Late Night with Jimmy Fallon to do ‘I’m On a Boat

The Roots and Fallon are also featured in the show’s ongoing Classroom Instruments segment. The Internet eats it up.

June 3, 2016: Popstar is released

Although the box office results remain uncertain, perhaps comedy guru Judd Apatow and the group returning to their musical routes have conspired to make this by far the biggest critical success of the band’s career so far, at least in terms of movies.

“Popstar is arguably the best thing the Lonely Island have ever made, and it’s also arguably the most Lonely Island–y thing they’ve ever made, too,” writes Jesse David Fox. “All of the Lonely Island hallmarks are there: the editing, the parody of masculinity, the use of pop culture.”

Fox also contends that if the Lonely Island never made another movie or record again, the legacy would already be secure. For Internet comedy, that’s indisputable. 

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*First Published: Jun 3, 2016, 11:03 am CDT