The Lonely Island's Journey From Berkeley To Internet Stardom

When you think of the people who forever changed the art of comedy, many names might pop up: Richard Pryor, Monty Python, Joan Rivers, etc. However, you may not consider the unlikely candidate of three best friends who grew up together in Berkeley, California, later chasing careers in filmmaking until they all ended up working for "Saturday Night Live." There, they turned the fundamentals of Lorne Michaels' tried-and-true television program on its head, adapting it for our modern age, and ultimately becoming the trifecta leading a comedy empire.

Those three friends were Akiva Schaffer, Andy Samberg, and Jorma Taccone. Samberg is likely the most recognizable of the three. He's been a cast member on "Saturday Night Live" for seven seasons before transitioning into a successful acting career with his Fox/NBC sitcom "Brooklyn Nine-Nine," film projects like "That's My Boy" and "Palm Springs," and animated films like "Hotel Transylvania," "Cloudy With a Chance of Meatballs," and "Storks." Schaffer and Taccone have also had successful careers in showbiz, with Taccone guest-starring in TV shows like "Girls" and "Parks and Recreation" and both creatives taking on work behind the camera.

However, the three are most impressive when their powers combine. Together, they're The Lonely Island, an iconic tentpole in modern comedy who shepherded in the era of viral videos and mainstream Internet humor. Whether producing endearingly profane music videos or ridiculous parody films, The Lonely Island has had an incredible journey to become a comedy juggernaut. As is always the case, though, The Lonely Island came from humble beginnings.

Akiva Schaffer and Jorma Taccone were the first of the trio to meet at Willard Junior High School, where they fell in love at first sight during a Spanish class. Their friend group later expanded to include Samberg, a year younger than them, as well as several other friends who all shared the same sense of humor. As Taccone described to The Movable Fest, they were "compiling friends into this big group of stupid dudes."

Sadly, the central trio of Schaffer, Taccone, and Samberg went their separate ways for college, with Taccone and Schaffer attending school in California while Samberg transferred to New York University. While Schaffer and Samberg pursued film degrees, Taccone studied theater at UCLA, whilst simultaneously maintaining his friendship with his friends from home over the phone. After graduation, the trio all reunited in their hometown of Berkeley, California, before ultimately deciding to give Hollywood a shot and move to Los Angeles together. Unbeknownst to them, this would eventually result in their cross-country journey to 30 Rockefeller Plaza.

Berkeley remains home to The Lonely Island, though they all live in separate cities. The trio eventually returned to their hometown with comedian Neal Brennan for a reality TV parody titled "Home for the Weekend," revisiting some of their old haunts whilst simultaneously dodging the revelation that their hit songs were written by a fifth grader. 

Upon arriving in Los Angeles in 2000, Akiva Schaffer, Andy Samberg, and Jorma Taccone moved into a small apartment with two other friends, one of whom, named Matt Bettinelli-Olpin, was a musician. Their initial plan for Hollywood was to create short films, but they quickly began collaborating with Bettinelli-Olpin on short comedy songs, deciding to upload them to the internet on various sites like iFilm.

One of their first songs, "Ka-Blamo!," was entirely written, filmed, and edited by the trio, as well as being their first foray into what they would proceed to call "fake rap." Their comedic style was already fully formed, and in an interview for The Los Angeles Times, hip-hop artist J-Zone described the trio's musical humor as "sharper than a lot of the serious guys I've worked with." Back then, they released music under the moniker "Incredibad," which would eventually become the title of their first official album.

When they began uploading content to their own website, they adopted the name "The Lonely Island" after an inside joke about the apartment they shared together. "Ka-Blamo!" was soon followed up by "Just 2 Guyz," which starred a monotone-singing Taccone and Schaffer as the titular guys, featuring a cameo from Samberg that eventually caught the attention of his future wife. However, their early internet content would soon reap rewards for the trio much sooner than Samberg's meet-cute, as they quickly set their sights on making Hollywood power plays. 

Between taking temp jobs in Los Angeles as production assistants and securing agents, The Lonely Island tried creating longer-form content. They produced several pilots for a "The Lonely Island" TV series, which was eventually purchased by Comedy Central. It never aired. The trio eventually crossed paths with Dan Harmon and Rob Schrab, who at the time ran a monthly short film festival called Super Midnight Movie Show, which would later become Channel 101.

For Super Midnight Movie Show, The Lonely Island created a soap opera parody titled "The 'Bu," which garnered the group attention at festivals. They eventually got a pitch meeting at Fox, where they showed executives "Just 2 Guyz," which persuaded Fox to give the guys a shot at producing a pilot. That pilot became "Awesometown," a sketch program that was meant to heavily feature Schaffer, Samberg, and Taccone. The pilot features an additional episode of "The 'Bu," in 3D.

The "Awesometown" pilot also included "Glirk," a sketch about an alien trying to convince a stranded astronaut to have sex with him, which was later brought over to "Saturday Night Live" with guest host Jack Black. There was also "Castaways," a recurring sketch featuring the trio as Tom Hanks-esque islanders. Sadly, Fox eventually passed on the series, as did MTV and Comedy Central, but the pilot is still watchable on The Lonely Island's YouTube channel.

Although "Awesometown" never made it past a pilot, it increased their notoriety in comedy circles, eventually landing them a job writing for the 2005 MTV Movie Awards. The ceremony's host Jimmy Fallon in particular was charmed by the trio's humor and recommended their online content to the likes of "SNL" producer Lorne Michaels and head writer Tina Fey.

Schaffer, Samberg, and Taccone all auditioned for "Saturday Night Live," which was the moment of truth for the three and their brand of humor (Samberg even told Howard Stern he threw up beforehand). However, Samberg got a laugh out of Tina Fey with his impression of Jimmy Fallon at a funeral, as well as a character called "Out-of-Breath Jogger From The '80s," which Samberg ended up reprising on the show in front of none other than Paul McCartney, which just goes to show how far they had already come with their goofiness.

Thankfully, Samberg didn't have to leave his Berkeley friends behind, as Taccone and Schaffer were both hired as writers. Nevertheless, the trio struggled to write and adapt to the "Saturday Night Live" formula for several weeks, which led to Taccone and Schaffer independently producing a music video titled "The Bing Bong Brothers," which became another viral hit and encouraged the writing duo to produce similar videos for the show.

The first video that The Lonely Island produced under the name "SNL Digital Short" was "Lettuce," which featured Samberg and castmate Will Forte having a dramatic conversation while taking huge bites out of heads of lettuce. Unlike most of the other sketches produced for "Saturday Night Live," the trio opted to produce "Lettuce" independently and pitch it to the show's producers fully edited and ready to air.

However, something changed by December 2005, only a few months into Samberg's tenure as a cast member and Taccone and Schaffer's time as writers. Together, the trio collaborated with cast member Chris Parnell to write and film "Lazy Sunday," a hardcore rap song about mundane activities like buying cupcakes and seeing "The Chronicles of Narnia: The Lion, the Witch and the Wardrobe." It wasn't until shortly before the live broadcast that the trio learned that "Lazy Sunday" would air on national television, but even they couldn't predict what would happen next.

As Samberg told The New York Times, "It definitely felt like something changed overnight," as the trio unknowingly tapped into a brand of humor that was unfamiliar to "Saturday Night Live" but was meant to thrive as a viral video. "Lazy Sunday" was uploaded to an infant YouTube after airing, became a global sensation, and turned Samberg from the show's latest unknown to its biggest up-and-comer. Although the creators expected the sketch's success to be a fluke, it was a turning point in the history of "SNL."

It wasn't long before the success of "Lazy Sunday" caught the attention of some big names in Hollywood. In spring 2006, "SNL" host Natalie Portman expressed her interest in doing a hardcore rap of her own, impressing the trio with her reciting of profane Lil' Kim lyrics. That sketch became "Natalie's Rap," which even received a sequel when Portman returned to host in 2018. "SNL Digital Shorts" eventually became a weekly occurrence, the most iconic including "Laser Cats," "People Getting Punched Just Before Eating," and "Dear Sister."

As if "Lazy Sunday" weren't a big enough hit, the trio was given the opportunity to top it when Justin Timberlake hosted "Saturday Night Live" in 2006, encouraged by Lorne Michaels to collaborate with the musical chops of The Lonely Island. That collaboration became "D*** in a Box," and the song was recorded, filmed, and edited in the span of two days and was only finished hours before the show was set to air. However, the sketch still had a huge hurdle to cross.

The premise of "D*** in a Box," as the title may suggest, finds Samberg and Timberlake as an R&B duo gifting their significant others with you-know-what for Christmas. Naturally, the sketch faced resistance from NBC's censors, as well as the Federal Communications Commission. The sketch was eventually bleeped for its live broadcast but gained further popularity when the uncensored version went to YouTube.

As quickly as The Lonely Island's success on "Saturday Night Live" was, they made an even quicker transition to filmmaking. "Hot Rod" began as a project for Will Ferrell that originated when the comedian was a cast member on "SNL" in the early 2000s. The script resurfaced at Paramount Pictures after the success of "Lazy Sunday" led Lorne Michaels to recommend the trio to take over the project. The Lonely Island supervised a rewrite of the film to better suit the group's comedic style, with Michaels telling Entertainment Weekly, "It's totally their movie, in every way."

The film centers on Rod Kimble, an Evel Knievel-wannabe who performs local stunts with his crew: half-brother Kevin (Taccone), amateur mechanic Dave (Bill Hader), and ramp builder Rico (Danny McBride). When his cruel stepfather, Frank (Ian McShane), is in need of a heart transplant, Rod decides to perform a ludicrous stunt to raise money for his surgery so he can finally beat Frank in a fight.

"Hot Rod" was released in 2007 to mediocre reviews and underperformed at the box office, but this wasn't unexpected for The Lonely Island. As Samberg told Vanity Fair in 2017, "We wanted to make stuff that people quote with their friends," which eventually led to the film's cult success over time. For the team behind "Hot Rod," that cult status — to be included among cult comedy classics like "Billy Madison" and "Wet Hot American Summer" — was worth the effort.

By 2009, The Lonely Island had accrued enough songs from producing "SNL" Digital Shorts to make an album. The group gathered in the summer of 2008 to write and produce songs for its debut album, "Incredibad." The first single, "J*** in My Pants," debuted on "Saturday Night Live" in 2008, although the song and music video were recorded and filmed before the season began.

Several other songs from "Incredibad" aired as "SNL" Digital Shorts, including "Space Olympics" and the Julian Casablancas-assisted "Boombox." Many of these became some of The Lonely Island's biggest and most meme-worthy hits, such as "Like a Boss," which popularized the use of the phrase on social media and internet circles. However, one of the tracks from "Incredibad" would see success that did not seem likely for The Lonely Island when they began making fake rap songs in Los Angeles.

That song was "I'm on a Boat," which features T-Pain accompanying Samberg and Schaffer on a yacht and bragging about their mundane and absurd nautical adventures. Like The Lonely Island's other musical Digital Shorts, it was a viral hit and meme gold. Still, even Schaffer, Samberg, and Taccone were surprised when it was nominated for Best Rap/Sung Collaboration at the 2010 Grammy Awards. As Samberg told TIME, "Having T-Pain on there helps tremendously," although the song eventually lost to Jay-Z, Kanye West, and Rihanna.

The start of The Lonely Island's second album cycle began in January 2011 with the "SNL" Digital Short "The Creep," featuring Nicki Minaj assisting the trio of Schaffer, Samberg, and Taccone in playing weirdos instructing listeners on how to creep on people. A few months later, they announced their sophomore album: "Turtleneck & Chain," officially released on May 10, 2011. During this year, they continued to release more "SNL" Digital Shorts featuring songs from their new album.

The tracks included the Mother's Day-themed "D*** in a Box" sequel "Motherlover," as well as their first collaboration with singer Michael Bolton, "Jack Sparrow." The album's biggest hit was "I Just Had Sex," which features Akon joining Samberg and Taccone singing cheerily about how excited they are to have had sex. Its music video, which premiered on "Saturday Night Live," also features cameos from Blake Lively and Jessica Alba as Samberg and Taccone's unimpressed lovers, respectively. 

"Turtleneck & Chain" went to No. 3 on the Billboard Top 200 chart and was the No. 1 U.S. Top Comedy Album of its year. It also received nominations at the Emmys and Grammys, continuing The Lonely Island's streak of recognition by prestigious award ceremonies for songs about poop, pop culture, and sex. The album is overall a continuation of what made "Incredibad" work, or as Schaffer told The AV Club, "I think we've recognized our strengths and our weaknesses, so that we can maybe play to them better this time around?"

By the end of Season 37 of "Saturday Night Live", The Lonely Island's tenure at the late-night sketch show was coming to an unfortunate close. Andy Samberg's penultimate episode of the season, hosted by Will Ferrell, featured the grand retrospective that was the "100th Digital Short," featuring returning characters like Shy Ronnie (Samberg) and the "D*** in a Box" singers, as well as celebrity cameos by Ferrell, Justin Bieber, Usher, Michael Bolton, Natalie Portman, and Julian Casablancas.

If that wasn't enough of a swan song for Samberg's seven years on "Saturday Night Live," his final episode also featured "Lazy Sunday 2," a reunion with Chris Parnell where the two rappers go see "Sister Act: The Musical" on Broadway. Samberg shared his final episode with fellow castmate and recurring Digital Short performer Kristen Wiig in 2012, while Taccone and Schaffer also took leave. However, a path forward for The Lonely Island would be hard-won, since the trio lived in different cities from one another post-"SNL" and were pursuing separate projects, including Samberg's "That's My Boy" with Adam Sandler that same year.

Schaffer, Samberg, and Taccone discussed the difficulty of continuing The Lonely Island in an interview with Splitsider, saying that though they don't have the luxury of a place to work together, "It's a priority for [them] to work together, for sure." Thankfully, fans of The Lonely Island's fake rap music wouldn't have to wait long after their "SNL" departure for a third album.

The third album by The Lonely Island is "The Wack Album," released in the summer of 2013. The new era for the comedy trio began when singer Adam Levine of Maroon 5 hosted "Saturday Night Live" in 2013 with musical guest Kendrick Lamar. Schaffer, Samberg, and Taccone returned to collaborate with both artists, debuting their song "YOLO" as their first "SNL" Digital Short following their official departure from the sketch show. They continued to put out singles from their upcoming album every week leading up to its release.

Among these were "Spring Break Anthem," a drunken party song and ode to same-sex marriage with a music video featuring cameos from Zach Galifianakis, James Franco, and Edward Norton. The Lonely Island teamed up with Robyn for the hypnotic club anthem "Go Kindergarten" and reunited with T-Pain for the mellow "I F***ed My Aunt." The album also included the previous "SNL" Digital Short song "3-Way (The Golden Rule)," which partnered Samberg and Timberlake's "D*** in a Box" duo with Lady Gaga. 

Around the release of "The Wack Album," The Lonely Island also played to its family-friendly strengths to feature on "Everything Is Awesome!," a song with Tegan and Sara for "The Lego Movie." The song was nominated for Best Original Song at the Academy Awards, and The Lonely Island performed on-stage with Tegan and Sara. Billboard described the performance as having "packed so much insanity into a minute and a half." 

Progress on The Lonely Island projects slowed down over the next few years, mainly due to Andy Samberg setting his sights on becoming a sitcom leading man with the Fox single-camera comedy "Brooklyn Nine-Nine." Premiering in 2013, the show stars Samberg as Jake Peralta, a childish NYPD detective amongst a supporting cast including Joe Lo Truglio, Stephanie Beatriz, Terry Crews, and Andre Braugher. The series was received with wide acclaim, with Samberg winning the Golden Globe for Best Actor for his performance in the show's first season.

Notably, the success "Brooklyn Nine-Nine" enjoyed hit a snag when Fox abruptly canceled the series in 2018 after its fifth season, before online fan outcry got the show renewed by NBC less than two days after its cancellation. The show concluded after a total of eight seasons, by the end accruing lots of praise for its depiction of LGBTQ+ characters and its tackling of topics like police brutality and sexual assault. 

Thankfully, Samberg wasn't completely separated from his The Lonely Island brethren. Taccone and Schaffer both directed episodes and guest-starred in episodes of the series. Samberg balanced work on "Brooklyn Nine-Nine" with occasional appearances on "Saturday Night Live," using his off-work time to collaborate with Schaffer and Taccone. The two wrote a sequel to "Natalie's Rap" when Portman returned to host "SNL" in 2018, with Samberg telling Vulture, "We will always try to be there for the show when we can."

Although The Lonely Island's first film was a box office bomb, the trio got a chance to redeem themselves with "Popstar: Never Stop Never Stopping," a mockumentary parodying musical documentaries like Justin Bieber's "Never Say Never." In the film, Samberg plays Conner4Real, a pop star whose career starts to decline when critics pan his latest album. He has to reckon with the breakup of his former boy band, The Style Boyz, whose members included Taccone as Connor's DJ, Owen, and Schaffer as Lawrence, who has retired to live on a farm.

The film, which also features supporting performances from Tim Meadows, Sarah Silverman, and Chris Redd, was released in June 2016 alongside an accompanying soundtrack. The soundtrack includes many songs from the film, such as the Adam Levine-assisted "I'm So Humble," the equality anthem "Equal Rights" with Pink, and the Schaffer-led "Things in My Jeep" featuring Linkin Park. Another song featured in the movie, "Finest Girl (Bin Laden Song)," debuted as a Digital Short on "Saturday Night Live" to promote the film.

Sadly, the reception of "Popstar: Never Stop Never Stopping" was similar to that of "Hot Rod." Although critics commended its comedy genius and potential to be a cult hit, the film underperformed at the box office, making back less than half its budget. Thankfully, The Lonely Island is used to this, with Taccone's previous directorial debut, "MacGruber," similarly underperforming before slowly gaining success as a cult film.

Michael Bolton reunited with The Lonely Island after the success of "Jack Sparrow" for a musical cameo at the end of "Popstar: Never Stop Never Stopping," joining The Style Boyz's reunion concert in their song "Incredible Thoughts." However, the relationship between Bolton and the group has been consistent since "Jack Sparrow." Akiva Schaffer told Vanity Fair that the four "go out for drinks or lunch or something" several times a year.

Having continuous conversations with Bolton eventually led to early talks about doing a Netflix special with the singer, which eventually turned into "Michael Bolton's Big, Sexy Valentine's Day Special," which was released in 2017. The mock telethon centers on Bolton, tasked by Santa Claus to encourage couples to make as many new babies in time for Christmas as they can. Schaffer co-directed the special alongside "Comedy Bang! Bang!" creator Scott Aukerman, and each member of The Lonely Island makes cameos throughout, with Samberg appearing as Bolton's arch-nemesis, Kenny G.

Publications like The Atlantic praised the special for "fully [embracing] the heightened, golden-maned character of Bolton" established way back in the "Jack Sparrow" Digital Short. In fact, the "Turtleneck & Chain" cut gets a sweeping piano rendition in the special, reminding audiences of the lasting power that The Lonely Island's humor has had, even six years later. For The Lonely Island fans, Michael Bolton's Valentine's Day special is a must-watch every year. 

In 2018, The Lonely Island fulfilled a long-awaited request from their fans: a live concert. The trio appeared at Clusterfest to perform some of their greatest hits, including guest appearances from Chris Parnell for "Lazy Sunday," as well as Michael Bolton and a Justin Timberlake puppet. However, the highlight of the evening for some was the debut of several songs featuring Samberg and Schaffer as Jose Canseco and Mark McGwire, the Oakland Athletics players known among baseball fans as the "Bash Brothers."

As it turns out, this was a prelude to something greater in the works from The Lonely Island. In 2019, they surprise-dropped "The Unauthorized Bash Brothers Experience" on Netflix. It's a visual album depicting the rise and fall of the Bash Brothers. Taccone, although attached as a producer and appearing in a cameo as Joe Montana, was less involved with this than other The Lonely Island productions, while Samberg and Schaffer wrote the songs together on days when Samberg wasn't working on "Brooklyn Nine-Nine."

The visual album was also made available on streaming services, including the track "IHOP Parking Lot" featuring Maya Rudolph and Haim. The Haim sisters in particular are longtime friends of The Lonely Island, with Taccone having previously appeared in the music video for the band's 2013 single "The Wire." Nevertheless, the special and album showed that The Lonely Island was adapting to the modern music era.

While "Everything Is Awesome!" was the trio's first foray into family-friendly work, they'd continue to branch out with future projects. One of those was their project with Disney, "Chip 'n Dale: Rescue Rangers," which was released on Disney+ in 2022. Akiva Schaffer was the first one attached to the film after he signed on to direct, recruiting Samberg and former "Saturday Night Live" writer John Mulaney to play the titular roles of Chip and Dale, respectively. Meanwhile, Taccone only contributed voicework in minor roles, including a cameo appearance as Batman. 

The film was notably popular on the internet for lambasting Hollywood reboots, featuring cameos from lower-tier animated characters, including Ugly Sonic (based on his appearance in the first trailers for 2020's "Sonic the Hedgehog" film), as well as Seth Rogen reprising his roles as live-action Pumbaa from 2019's "The Lion King," Master Mantis from "Kung Fu Panda," and B.O.B. from "Monsters vs. Aliens." Schaffer described the film in an interview with the San Francisco Chronicle as "a love-letter celebration of animation." 

Critics seemed to enjoy The Lonely Island's take on the "Chip 'n Dale" franchise, with some alleging that "'Rescue Rangers' is engineered for older audience members" rather than a new generation of kids (via Detroit News). Still, it shows that the strengths of The Lonely Island don't just apply to films or music that's meant to shock and appall audiences rather than delight and humor them.

It's been a good few years since The Lonely Island has properly reunited for a musical project, with "The Unauthorized Bash Brothers Experience" being the group's most recent collaboration. However, the members have not shied away from working together behind the scenes, appearing as guests on one another's projects and producing together. The trio helped develop films like Kyle Mooney's "Brigsby Bear" as well as Samberg's 2020 romantic comedy "Palm Springs," which he starred in alongside Cristin Milioti.

In the world of TV, The Lonely Island also co-produced the Hulu series "PEN15," created by Maya Erskine and Anna Konkle, who star as pubescent versions of themselves. The trio has also been heavily involved with their former "SNL" co-worker Tim Robinson's Netflix sketch series "I Think You Should Leave with Tim Robinson," on which Schaffer worked as a director and Samberg guest-starred in a first-season sketch. 

The Lonely Island's most recent work is "Digman!," an animated series co-created by Samberg, who also stars as the series' titular archaeologist and adventurer. During the press junket for the series, Samberg told /Film about the future of The Lonely Island, claiming the desire to make music together is still there, albeit "between kids, and Jorma [living] on the East Coast, and projects and eight years of 'Brooklyn Nine-Nine,' we're doing our best. But it has been hard." Hopefully, the time will come for The Lonely Island to reunite and bless the world with more brilliantly stupid comedy.