Group members Andy Samberg, Akiva Schaffer and Jorma Taccone began creating live skits, comedy shorts and music parodies together in the early 2000s, having met the previous decade, during their high school years.

[2] Two musical shorts created by the group for the show, "Lazy Sunday" and "Dick in a Box", gained popularity on the Internet and garnered much media attention.

[1] The Lonely Island's 2008 single "Jizz in My Pants" later became the group's first entry on the United States Billboard Hot 100 record chart, where it peaked at number 72.

[5] "I'm on a Boat", the album's third single, peaked at number 56 on the Billboard Hot 100 and was nominated for Best Rap/Sung Collaboration at the 2010 Grammy Awards.

[4][8] "I Just Had Sex", the album's first single, peaked at number 30 on the Billboard Hot 100 and received a platinum certification from the RIAA.