Samberg, who would also end up an SNL cast member, originally met Schaffer and Taccone in Berkeley, California while attending junior high school. After graduating high school, the three went their separate ways. They reunited in 2001, formed the Lonely Island, and created sitcoms and sketch shows in hopes of landing a network deal. It didn't happen, but when they partnered with the Internet site Channel 101, their popularity took off. A faux hip-hop project called Incredibad followed, then the Fox network commissioned a sketch show called Awesometown from the crew, but it never made it past the pilot.

After being hired by SNL, a 2005 digital short they created called Lazy Sunday became an online phenomenon. Featuring Samberg and fellow cast member Chris Parnell, Lazy Sunday would spawn the phrase "Mr. Pibb and Red Vines = Crazy Delicious" and be followed a year later by the equally popular short Dick in a Box starring Justin Timberlake. That same year they made a moderately successful jump to the big screen with the film Hot Rod. The year 2008 saw them take on the Euro-dance sound with a new short, Jizz in My Pants. The track was made available as a digital download in order to promote the group's full-length debut. Once again titled Incredibad, the album was scheduled for an early 2009 release and featured guest stars like Timberlake, Norah Jones, and T-Pain. Timberlake would return for their sophomore release, Turtleneck & Chain. Beck, Snoop Dogg, and Rihanna would also land on the 2011 album, along with the power ballad king, Michael Bolton.

Their next effort, The Wack Album, which featured guest spots from Too $hort, Kendrick Lamar, and Lady Gaga, arrived in 2013. That same year, Samberg joined the sitcom Brooklyn Nine-Nine while the group joined Tegan and Sara for 2014's "Everything Is Awesome," the theme from The Lego Movie produced by Devo's Mark Mothersbaugh. In 2016 they wrote, directed, starred in, and released the film Popstar: Never Stop Never Stopping, a mockumentary that seemed to be referring to Justin Bieber. The film was produced by Judd Apatow and featured an accompanying soundtrack from the Lonely Island. ~ David Jeffries