The Comedy Team of the 21st Century

Comedy teams go back to the early days of comedy and vaudeville with acts such as Stan & Ollie, Abbott and Costello, and George and Gracie. Comedy teams can come in duos, trios, or large ensembles, sometimes referred to as troupes. In the 2000s, a comedy trio on Saturday Night Live would make comedy history by revolutionizing the sketch-comedy format. That trio is “The Lonely Island,” a comedy team consisting of Andy Samberg, Jorma Taccone, and Akiva Schaffer. Their “Digital Short” series on SNL, which included absurdist prerecorded sketches and music videos for original comedy songs, introduced the show to the digital age and gave it new cultural relevance online. Their subsequent work outside of SNL, which includes films such as Hot Rod and Popstar: Never Stop Never Stopping, and television series such as Brooklyn 99, followed their signature style of meta-absurdist humor. “The Lonely Island” was simultaneously ahead of its time and also met its moment and, in many ways, set the tone for comedy in the 21st century. 

Andy Samberg, Jorma Taccone, and Akiva Schaffer first met in Berkeley, California, while they were in middle school. They quickly bonded over their shared love of humor and the arts, which all three planned to pursue after college. The trio stayed in touch during their college years, with Samberg and Schaffer both studying film and Taccone studying theater. After graduating from college, the three reunited and decided to move to L.A., where they began making comedy videos and posting them online. They named themselves “The Lonely Island” as that was what they called their L.A. apartment at the time. While living in L.A., the trio worked various production assistant jobs in television and shopped around their original show ideas. Although none of those early projects materialized into network TV deals, they did develop a reputation in the local comedy scene and had their first big break when they were recruited by Jimmy Fallon to write for the 2005 MTV Movie Awards, which Fallon hosted. Fallon’s silly musical style of comedy blended perfectly with The Lonely Island, and Fallon was so impressed with the trio that he convinced Saturday Night Live producer Lorne Michaels and then head writer Tina Fey to let the group audition for the show. Andy Samberg was hired as a cast member while Schaffer and Taccone were hired for the show’s writing staff. 

The trio initially struggled to get their sketches on air, and they began to feel that their comedic sensibilities were not a fit for Saturday Night Live. It was then that The Lonely Island decided to create “The SNL Digital Short.” Now, Saturday Night Live has always had pre-recorded segments, and sometimes even short films since its premiere in 1975. In fact, season one of the show featured several short films that were directed by comedian and filmmaker Albert Brooks. In the late 1980s, Ben Stiller also contributed short films to the show while serving as a cast member. Still, Lonely Island’s Digital Shorts were unique in that it was the mid 2000s, and the internet was slowly becoming a prevalent platform for short-form comedy videos. Early Digital Shorts such as “Lettuce” and “Lazy Sunday” became viral sensations online. In the 1990s, SNL had a historically difficult time with fluctuating ratings and popularity. With the internet on the rise and more short-form comedy content available than ever before, many were skeptical about how SNL would adapt to the new digital landscape.  Through their Digital Shorts, The Lonely Island provided SNL with the perfect opportunity to reach the internet, which led to a massive renewal of its cultural relevance. 

The Lonely Island continued to create more hit Digital Shorts. They quickly became a staple of the show. Fans would look forward to the Digital Shorts, and celebrity guests wanted to be a part of them. “Natalie Raps,” featuring Natalie Portman, was another huge viral internet success. And perhaps the most well-known digital short of them all came in 2006, when Justin Timberlake and The Lonely Island introduced the world to “Dick in a Box,” one of the most memorable and popular sketches in the show’s history. Other popular Digital Shorts include “I’m On A Boat”, “Boombox” featuring The Strokes frontman Julian Casablancas, and the “Laser Cats” series. In 2012, the trio commemorated their 100th Digital Short by bringing back their most iconic characters and videos in one hilarious music video. 

The trio has continued to work together outside of their work on SNL. In 2007, The Lonely Island released Hot Rod, which features Andy Samberg as wannabe stuntman Rod Kimble. Jorma Taccone also stars as Rod’s stepbrother and best friend, Kevin, and Akiva Schaffer made his directorial debut with the film as well. While not a commercial success upon its initial release, Hot Rod has amassed a large cult following in the years since and ranked number two on my Top 10 Comedy Movies of the 2000s list. Since leaving SNL, the trio has continued to collaborate on projects and has also branched out to work on various projects in film and television on their own. The trio would once again reach cult status in 2016, when they created Popstar: Never Stop Never Stopping, a musical mockumentary following pop star “Conner4Real,” played by Andy Samberg. Popstar was directed by Taccone and Schaffer, and both of them also star in supporting roles. The trio has also had many of their songs from their comedic videos released on albums. Lifelong fans of the Oakland A’s, in 2019, the trio created The Unauthorized Bash Brothers Experience for Netflix, a collection of shorts similar in style to their SNL Digital Shorts that serves as a humorous tribute to the team. Andy Samberg has continued his career as an actor, appearing in movies such as Palm Springs and the animated Hotel Transylvania franchise, as well as the hit sitcom Brooklyn 99. Taccone and Schaffer have continued to direct comedy movies, including MacGruber and the 2025 reboot of The Naked Gun. Together with Seth Meyers, The Lonely Island also hosts a podcast, “The Lonely Island and Seth Meyers Podcast”, in which they commentate and analyze their past Digital Shorts and give behind-the-scenes stories about the production of the videos.

It has been over twenty years since The Lonely Island joined Saturday Night Live, and they are not only still working and making some of the best comedies of the past few decades, but also still working together frequently and remaining good friends. Historically, that is not always a given for comedy teams. Their legacy is more than just being SNL legends. The absurdist tone of their comedy can be seen in much of today’s comedy, and the role of pre-recorded segments on SNL has only expanded since the trio’s departure. But perhaps the real legacy of The Lonely Island is the mark they left on “internet comedy.” Not only were they able to bridge the gap between legacy media and new media in the early days of the internet, but they also gave young comedians and creators a blueprint for taking risks and producing content for the internet to showcase their unique styles and comedic sensibilities.