Most comedians have had a pretty conventional path to show business and it usually involves a theater stage, a comedy club or an improv class, but comedy trio the Lonely Island was one of the earliest examples of comedians who rose to fame because of the internet. Now founding members Andy Samberg, Akiva Schaffer and Jorma Taccone are some of the biggest actors, writers and directors in Hollywood.

Berkeley, California-born Andy Samberg was a student at UC Santa Cruz before transferring to Tisch School of the Arts at New York University. In college, creative writing was Samberg’s best and favorite subject, while he majored in experimental film at Tisch. Samberg, fellow UC Santa Cruz grad Akiva Schaffer and UCLA grad and theatre student Jorma Taccone were all childhood friends in California who separated for a time during their college years but reunited in Berkeley after graduating with a plan to make their way into the entertainment industry. One of the things they did during their free time was make funny internet videos. Schaffer came up with the idea to call their website “thelonelyisland.com” as a reference to the nickname for the low-rent L.A. apartment where Samberg, Schaffer and Taccone often hung out while improvising comedic rap songs.

YouTube didn’t exist until 2005, but before that, a short film festival called Channel 101 which was launched in 2002 by Dan Harmon and Rob Schrab ended up being the first place where their videos became popular. A parody of FOX drama The O.C. called The ‘Bu (the title being a nickname for Malibu) was their most popular series of short films and the popular reception they got led to the trio of comedians receiving attention from talent agents. Although none of their network pitches or pilots went anywhere and their ideas for TV shows were rejected by FOX, MTV and Comedy Central. However, fortune came when a writing gig for the 2005 MTV Movie Awards led that show’s host Jimmy Fallon to recommend the trio to Saturday Night Live creator Lorne Michaels, who hired the trio as writers for SNL and Andy Samberg as a cast member that same year (which, again, also happened to be the same year YouTube was founded).

On SNL, the Lonely Island’s claim to fame was the pre-recorded SNL Digital Shorts, which existed on the show before the trio got hired (SNL writer Adam McKay is the one credited for creating them) but they received a new level of popularity thanks to Samberg, Schaffer and Taccone’s involvement. “Lazy Sunday” (2005), which was a Digital Short starring Samberg and SNL castmate Chris Parnell in a hip hop video about their quest to see Disney’s Chronicles of Narnia film was an early hit, while Natalie Portman rapping in the Digital Short “Natalie’s Rap” (2006) was also popular, along with the deliberately cheap and humorously haphazard “Laser Cats!” (2006) and the satirical music video “Dick in a Box” (2006) in which Samberg stars alongside Justin Timberlake (and which is still by far the most popular one). That video has since become a widely praised sketch and Christmas song and it even won the Emmy for Outstanding Original Music and Lyrics in 2007. Other popular SNL Digital Shorts by the Lonely Island include “Jizz in my Pants,” “I’m on a Boat,” “Like a Boss!,” the Mother’s Day-themed “Motherlover,” “Shy Ronnie,” “I Just Had Sex,” “Jack Sparrow,” “3-Way (The Golden Rule)” and “YOLO.” Aside from Timberlake, the trio has collaborated with other musicians in these shorts like T-Pain, Rihanna, Julian Casablancas, Katy Perry, Akon, Nicki Minaj, Michael Bolton and Lady Gaga.

Samberg starred in most of these shorts, Schaffer directed most of them and Taccone produced the music, often with his brother Asa Taccone. The Lonely Island has made over 100 Digital Shorts for SNL from 2005 to the present day, including the 2025 short they made for the SNL 50th Anniversary Special called “Anxiety.”

The popularity of these shorts on both SNL and YouTube has led to four albums that featured many of their most popular songs. Those albums are Incredibad (2009), Turtleneck & Chain (2011), The Wack Album (2013) and The Unauthorized Bash Brothers Experience (2019) which was the accompanying comedy rap album to the 2019 Netflix special of the same name. They had teamed up with Netflix two years earlier when they created Michael Bolton’s Big, Sexy Valentine’s Day Special, a silly but funny affair that of course also featured a lot of music.

Following the success of SNL, the trio would collaborate and work separately on various films and TV shows, including the cult hit comedy Hot Rod (2007) directed by Schaffer and starring Samberg as an accident-prone stuntman. Originally conceived without the Lonely Island’s involvement as a vehicle for Will Ferrell, it eventually fell through in development and Lorne Michaels convinced Paramount to let the Lonely Island make it. It flopped and received mixed reviews, but comedy fans and Lonely Island devotees still appreciated the film’s humor and still do to this day.

Lorne Michaels also produced Jorma Taccone’s action comedy MacGruber (2010) starring Will Forte in a feature film adaptation of his recurring SNL sketch, but that was also a poorly reviewed box office flip (also with a cult following). After both directing flops, Schaffer and Taccone co-directed, co-wrote and co-starred with Andy Samberg in the mockumentary Popstar: Never Stop Never Stopping (2016). You’ll never guess what happened to it at the box office. Even with producer Judd Apatow behind it, it still managed to bomb (maybe the Lonely Island’s sense of humor doesn’t click with mainstream audiences as well as internet audiences) but unlike their other films, Popstar received mostly positive reviews and I personally found the film hilarious, so once again the films may lose but comedy fans win.

The Lonely Island trio would also produce SNL cast member Kyle Mooney’s indie comedy Brigsby Bear (2017), the highly acclaimed sci-fi rom-com Palm Springs (2020) starring Samberg, Cristin Milioti and J.K. Simmons, Kris Rey’s indie film I Used to Go Here (2020) starring Gillian Jacobs and Jemaine Clement, and Jake Johnson’s silly but sincere comedy thriller Self Reliance (2023) starring Johnson and Anna Kendrick. They also teamed up with Paul Scheer to create the short-lived FOX sketch comedy series Party Over Here (2016) starring comedians Nicole Byer, Jessica McKenna and Alison Rich, they produced Andrea Savage’s truTV sitcom I’m Sorry (2017-19), Esther Povinsky’s Freeform sitcom Alone Together (2018), Maya Erskine and Anna Konkle’s Hulu comedy PEN15 (2019-21), Tim Robinson’s Netflix sketch comedy series I Think You Should Leave with Tim Robinson (2019-23) and the animated Comedy Central sitcom Digman! (2023-present) co-created by and starring Samberg as an archaeologist named Rip Digman (SNL fans may notice Samberg’s voice is Nicolas Cage-inspired).

As the most famous member of the group, Andy Samberg has received the most acting opportunities. He played the lead role in the NYPD workplace comedy Brooklyn Nine-Nine which ran for eight seasons from 2013 to 2018 on FOX and from 2019 to 2021 on NBC. That series received critical acclaim as well as a Golden Globe.

Plus Samberg had guest roles on popular shows like Arrested Development, The Sarah Silverman Program, Parks and Recreation, Adventure Time, Portlandia, 30 Rock, SpongeBob SquarePants, the British sitcom Cuckoo, Comedy Bang! Bang!, The Eric Andre Show, New Girl, Master of None, Bob’s Burgers, The Dark Crystal: Age of Resistance and Never Have I Ever as well as films like I Love You, Man (2009), Cloudy with a Chance of Meatballs (2009), Friends with Benefits (2011), Celeste and Jesse Forever (2012), the Hotel Transylvania series (2012-22), Storks (2016), Chip ‘n Dale: Rescue Rangers (2022), Spider-Man: Across the Spider-Verse (2023) and the British war drama Lee (2023) opposite Kate Winslet. Gamers may have also heard his voice in Gearbox Software’s 2022 Borderlands spin-off video game Tiny Tina’s Wonderland.

Akiva Schaffer has directed Disney’s Chip ‘n Dale: Rescue Rangers, which starred John Mulaney and Andy Samberg as the voices of Chip and Dale, and that film ended up winning an Emmy. The Roger Rabbit-style film, which famously starred Ugly Sonic as one of Chip and Dale’s fellow toons, apparently bared no ill will from Sonic the Hedgehog distributor Paramount because that studio immediately hired Schaffer to direct The Naked Gun (2025), a legacy sequel starring Liam Neeson as the son of Leslie Nielsen’s character Frank Dreben. Both Chip ‘n Dale: Rescue Rangers and The Naked Gun received positive reviews.

As for Jorma Taccone’s solo efforts, he continues doing work both behind the scenes and in front of the camera. He co-created the 2021 MacGruber spin-off series on Peacock with Will Forte and John Solomon, he co-produced the TBS comedies The Last O.G. and Miracle Workers, he directed episodes of Parks and Recreation, Up All Night, Brooklyn Nine-Nine, The Last O.G., Miracle Workers, MacGruber and Knuckles, and he has executive produced the critically adored indie film The Diary of a Teenage Girl (2015) starring Bel Powley. Taccone has also had acting roles in films like The Lego Movie (2014), David Sandberg’s martial arts comedy Kung Fury (2015), Spider-Man: Into the Spider-Verse (2018), The Lego Movie 2: The Second Part (2019), An American Pickle (2020), Weird: The Al Yankovic Story (2022), Spider-Man: Across the Spider-Verse (2023) and Sonic the Hedgehog 3 (2023) as well as the TV shows Up All Night, Girls, The League, Gravity Falls, Parks and Recreation, Man Seeking Woman, Brooklyn Nine-Nine, Drunk History, Miracle Workers, Bless the Harts and Knuckles.