Andy Samberg Apologized to T-Pain After 'I'm on a Boat' Got a Grammy Nomination
Andy Samberg Apologized to T-Pain After 'I'm on a Boat' Got a Grammy Nomination

Published: May 27, 2025

Andy Samberg and his The Lonely Island bandmates opened up on their podcast about one of their biggest hits, "I'm on a Boat." The song was nominated for best rap/sung collaboration, which the bandmates felt uncomfortable about, they said. Samberg remembered apologizing to T-Pain for the song's nomination, telling the rapper he felt the song was only nominated because The Lonely Island is White.

The Lonely Island's "I'm on a Boat" became a smash hit, but there was one thing that irked Andy Samberg about it: Its Grammy nomination. Samberg and his bandmates Jorma Taccone and Akiva Schaffer spoke with Seth Meyers about the song on the May 27 episode of The Lonely Island and Seth Meyers Podcast. The song "I'm on a Boat" was featured on The Lonely Island's debut album Incredibad, which was released in February 2009.

Taccone does not feature on the song, because Samberg and Schaffer wrote it while he was out of town. But the song does feature T-Pain. A year after the song - and its over-the-top music video - premiered on the Feb. 7, 2009, episode of Saturday Night Live, the band and T-Pain were unexpectedly nominated for the Grammy for best rap/sung collaboration (now titled the Grammy for best melodic rap performance).

Samberg, 46, and Schaffer, 47, went to the Grammys and had a "blast," Schaffer said, noting he ever wore his tuxedo from the video. "We were nominated under best rap sung collaboration against songs like 'Run This Town,'" he said, referencing the blockbuster collaboration between JAY-Z, Rihanna, and Kanye West. That track ultimately won, Samberg noted, adding, "thank God."

"I don't know if anyone's ever gone to the Grammys hoping to lose more," Schaffer added. "We were like, 'If we win, we can't get on stage.' We were only confident enough to go because we were that sure that we were going to lose." Meyers, 51, agreed that if they had won, it "might have been a weird tipping point that you wouldn't have recovered from."

Samberg said they were "a little salty" about not being nominated for best comedy album because they had the best-selling comedy album of the year. He joked, "And as everyone knows, if you sell a lot, that means it's high quality."

Samberg remembered that once they made it to the Grammys, they "bumped into T-Pain" and "were so excited to see him." And before he said anything, we were like, 'I know. I know,'" Samberg said. "He's like, 'Dude.' Because we hadn't talked since we got nominated. And we were like, 'Oh, man. This is not a good look.'"