Digital Shorts were the creation of cast member Andy Samberg and the writers Akiva Schaffer and Jorma Taccone. They went to high school together in Berkeley, California, and after college they got together as a comedy collective called The Lonely Island. Pre-YouTube, they make quirky, low-budget videos and posted them on their website. Saturday Night Live
hired them in 2005, and that season they had a breakout with "Lazy Sunday
," one of the first videos to go viral on YouTube, which launched earlier that year. Empowered with bigger budgets and more airtime, they kept the Shorts coming, and started attracting celebrities, starting with Natalie Portman, who starred in "Natalie's Rap" later that season.
"Dick In A Box" came in The Lonely Island's second season on the show. By this time, their Digital Shorts were the showstoppers, and getting someone like Justin Timberlake on board was an easy sell. NBC posted the videos on nbc.com and they showed up all over YouTube. The YouTube versions would often get taken down and reposted until NBC put it up on their official channel in 2018.
The Lonely Island managed to retain their self-effacing humor and underdog attitude. In 2009, they included "Dick In A Box" on their first album release, Incredibad