"I'm on a Boat" is a single from The Lonely Island's debut album Incredibad. It was also featured as a Saturday Night Live Digital Short. The song features R&B singer T-Pain. The song, produced by Wyshmaster, is a parody of many rap video clichés, especially the music video for the Jay-Z song "Big Pimpin'." The music video reached number one on YouTube in February 2009 and was number one on the US iTunes music video chart. The song was nominated for Best Rap/Sung Collaboration at the 52nd Grammy Awards. The Lonely Island has also performed the song live on Late Night with Jimmy Fallon with Black Thought filling in for T-Pain. The trio also performed an altered clean version for a "Classroom Instruments" segment on The Tonight Show Starring Jimmy Fallon. The song went platinum.

Akiva Daniel Shebar Schaffer is an American actor, filmmaker, comedian, and musician. He is a member of the comedy group The Lonely Island along with childhood friends Andy Samberg and Jorma Taccone. Schaffer began his career with The Lonely Island making videos for Channel 101. In 2005, Saturday Night Live hired the trio, with Schaffer joining as a writer. In their time at SNL, The Lonely Island pioneered the digital short format, creating some of the most popular sketches of all time, including "Lazy Sunday", "I Just Had Sex", "I'm on a Boat", and "Dick in a Box". After SNL, Schaffer went on to direct movies including Hot Rod, The Watch, Popstar: Never Stop Never Stopping, and Chip 'n Dale: Rescue Rangers. The Lonely Island has made albums such as Incredibad, Turtleneck & Chain, and The Wack Album. Schaffer also produced a number of TV shows and movies, some of which include MacGruber, PEN15, I Think You Should Leave with Tim Robinson, and Palm Springs.