Lonely Island members really wanted to lose Grammy for ‘I’m on a Boat’

The Lonely Island was not laughing when the group was nominated for a real Grammy in 2010.

That was the year the comedy trio of Andy Samberg, Akiva Schaffer, and Jorme Taccone were nominated for Best Rap/Sung Collaboration against serious heavyweights in the genre.

“I don’t know if anyone’s ever gone to the Grammys hoping to lose more,” Schaffer said on Tuesday’s episode of The Lonely Island and Seth Meyers Podcast. “We were like, if we win, we can’t get on stage. We were only confident enough to go cause we were that sure that we were going to lose.”

Meyers quipped, “You’re right, that might have been a a weird tipping point that you wouldn’t have recovered from.”

The video for the song showed the guys in their tuxes, as they were, well, out on the water. The very real rapper T-Pain performed alongside them, as they rapped about being on the deck with their boys, drinking champagne, and wearing their “flippy-floppies.” It was another of their videos that fit in nicely with “Threw It on the Ground” and “Jizz in My Pants.”

Their competition was stiff, songs that were not parodies but actual songs: Beyoncé and Kanye West’s “Ego”; West, Keri Hilson, and Ne-Yo’s “Knock You Down”; and T.I. and Justin Timberlake’s “Dead and Gone.” The winners were West, Jay-Z, and Rihanna for “Run This Town.”

“We were a little salty about not being nominated for comedy album,” Samberg said. He joked, “I believe we had had the biggest selling comedy album of the year and, as everyone knows, if you sell a lot, that means it’s high quality.”

The Saturday Night Live alum recalled that reluctant nominees ran into T-Pain on the red carpet.

“Before he said anything, we were like, ‘I know.’ He’s like, ‘Dude.’ Cause we hadn’t talked since we got nominated, and we were like, ‘Oh man, this is not a good look.’ And he was like, ‘You know how many songs I did this year? And this is the one that got nominated?’ We were like, ‘We know. We’re sorry. It’s cause we’re white.”

Schaffer emphasized that they hadn’t taken the nomination seriously.

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“We never for a second thought we’d win, which was, again, a relief and why we could take the whole day as kind of a fun joke that we were there as musicians,” he said, adding that he had worn the tux from the video.

Samberg had a message for “everyone else that had a good rap song collaboration that year: sorry.”

The group was Grammy-nominated two years later for Comedy Album for their Turtleneck & Chain, but they didn’t win then either.

Listen to the full conversation above.