Did Weird Al Yankovic really date Madonna?

Weird Al Yankovic is one of the most iconic musicians alive today. The comedian has had a fascinating life and career, making a household name for himself as a creator of hilarious parodies of beloved songs. Throughout his illustrious career, folks have remained intrigued by Weird Al’s personal life, which he has often kept private. But currently, people are debating if Weird Al ever dated Madonna, the iconic pop star who defined the 1980s pop scene.

Without a doubt, the pair are instantly recognizable in music with a strong repertoire of music which has long kept their respective fanbases kicking and completely entertained. That being said, it’s worth questioning if the duo ever actually dated each other. So, let’s dive in and explore these situation for ourselves.

What started this rumor?

This confusion was caused by a trailer for Weird: The Al Yankovic Story, a satiric biopic about Al’s life and career. However, unlike most biographies, Weird: The Al Yankovic Story encapsulates Al and his chaotic nature by being built around lies. Featuring loads of exaggerated and fictitious scenarios, the movie is basically a parody of the biographic genre. 

This new trailer features a scene where Weird Al and Madonna are making out after Madonna visits Al to ask if he plans to do a parody of her song “Like A Virgin.” But is this based on actual events, or is this totally made up for the movie?

Did Weird Al and Madonna date?

Weird Al and Madonna never dated in the real world. Like most of the movie, this is something totally made up for the film. In fact, it is unknown whether the pair has ever actually met in person. 

However, Al did parody “Like A Virgin,” turning it into “Like A Surgeon” on his 1986 album Dare to Be Stupid. The song was released as a single, and it peaked at number 47 on the Billboard Hot 10. Fascinatingly, Madonna did reportedly play a role in the song’s creation. She told a friend that she wondered when Al would turn “Like A Virgin” into “Like A Surgeon.” This friend was a buddy of Al’s manager Jay Levey. The person told Levey, and Levey told Al. And the rest is history. 

Al did “interview” Madonna during his 1985 TV special, Al TV 3, though it isn’t the type of interview you’d expect, and Al does ask Madonna questions no one else would dare to ask. And this interview did confirm that Madonna has never taken a bus trip to Boise, Idaho.

When talking about the movie to Parade, Al has said that he hopes Madonna is okay with her portrayal in the film. “I hope she thinks it’s funny.” Said Al. “She’s a big part of the movie, and I really, really hope she can take a joke. I think she can.”