‘Weird Al’ Yankovic Says He Quit His Mailroom Job When His Song Hit the Billboard Hot 100 After No One Wanted to Sign Him

Fame didn’t arrive overnight for “Weird Al” Yankovic. On Thursday’s Late Show with Stephen Colbert, he told the story of how the music business initially labeled his work as novelty material, unsure how to market a career built on parody.

Yankovic recounted the uphill climb through the late 1970s and early ’80s when labels repeatedly dismissed him despite recognizing his talent. He credited a turning point in 1983 with the success of a duet that helped him break into the mainstream.

At the time of his first chart appearance he was still pulling regular shifts at a mailroom job, earning only a few dollars an hour. He says he discovered his name on Billboard’s Hot 100 while sorting the post — and resigned that very day. “That was the day I gave notice!” he recalled.

The song that catalyzed his ascent was “Ricky,” a 1983 parody of Toni Basil’s “Mickey,” recorded as a duet with voice actress Tress MacNeille. Yankovic turned the upbeat power-pop hit into a humorous homage to I Love Lucy stars Lucille Ball and Desi Arnaz, and it proved to be the break he needed.

Decades later, Yankovic’s career shows no signs of slowing. This year he added 90 dates to his Bigger and Weirder tour, which already included a milestone: his first-ever sellout at Madison Square Garden, achieved 46 years into his career. He described walking the arena before the show and feeling awed by posters honoring icons like Elton John and Taylor Swift. “It’s the greatest venue in the world!” he said, delighting in the moment.

Yankovic also took part in a comedic cold open during the episode — a mock holiday message in which he humorously scolded audiences for mangling his name. “My last name is pronounced Yankovic, not Yanko-vich!” he joked, playfully defending his family’s heritage.

Watch Yankovic’s full interview with Stephen Colbert below.

Full Interview

Cold Open / Sketch

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