Andy Samberg and his comedy rap group, The Lonely Island, recently reflected on their surprising 2010 Grammy nomination for the song “I’m on a Boat” featuring T-Pain. The trio, which also includes Akiva Schaffer and Jorma Taccone, admitted they hoped to lose the award for Best Rap/Sung Collaboration. “I don’t know if anyone’s ever gone to the Grammys hoping to lose more,” Schaffer said.
“We were like, ‘If we win, we can’t get on stage.’ We were only confident enough to go because we were that sure we were going to lose.”
The Lonely Island found themselves nominated alongside major artists like Beyoncé, Kanye West, Jay-Z, and Rihanna. The award ultimately went to Jay-Z, Kanye West, and Rihanna for their collaboration “Run This Town.”
Samberg shared an awkward encounter with T-Pain at the Grammys, recalling, “He was like, ‘You know how many songs I did this year? This is the one that got nominated?’ We were like, ‘We know, we’re sorry.
Reflecting on Grammy nomination
It’s because we’re white!'”
The group acknowledged that their nomination might have been a fluke, considering the comedic nature of their song compared to the other nominees. They even joked about being “a little salty” about not being nominated for Best Comedy Album that year.
Despite the unusual circumstances, The Lonely Island enjoyed the experience as a “fun joke,” with Schaffer wearing the same tuxedo from the “I’m on a Boat” music video to the event. Samberg lightheartedly apologized to “everyone else that had a good rap song collaboration that year.”
T-Pain, who collaborated with the group on the song, went on to win a Grammy that night for his work on Jamie Foxx’s “Blame It” in the Best R&B Performance category. Looking back, The Lonely Island expressed relief at not winning the award, as they never expected to win in the first place.
The Grammy nomination for “I’m on a Boat” remains a memorable and humorous moment in the comedy trio’s career.
