How Madonna Debuted Dick Tracy With an All-Male Kickline

It is weird, I think, to not have strong feelings about Madonna. She’s been a major pop cultural presence since I’ve known what pop culture was and she seems custom-designed to elicit reactions, but I don’t feel especially strongly about her. Most people either love or hate her, and all of those lovers and haters would like nothing better than to discuss those feelings at length. I take a pass on that. Play a track from She’s So Unusual, and I’ll have a profound emotional reaction. Play a Madonna song from the same period, and I’ll say, “Oh, this Madonna. She is an Italian-American singer, 1979-present.”

I had to write about her this weekend, however, because her Blond Ambition World Tour kicked off twenty-five years ago today. Not knowing a single thing about it, I had to do some research and even scheduled a sit-down with a friend who has an encyclopedic knowledge of Madonna’s career. Today, at the very least, I can say with certainty that I know a hell of a lot more about Madonna in her prime.

From my nerd perspective, the most interesting thing I learned has to do with Madonna’s role as Breathless Mahoney in the 1990 film version of Dick Tracy. Madonna incorporated elements of the film and her album I’m Breathless into the Blond Ambition tour. But while the tour opened on April 13, 1990, the movie Dick Tract didn’t hit theaters until June 15, when Madonna had already performed all but seven of her U.S. stops. Consequently, a good number of American fans got their first glimpse of the re-envisioned Dick Tracy at the tour.

That was great marketing for the film, of course, but it also meant that the first glimpse of Dick Tracy was unusual, sexy and overtly gay — in short, pretty on-target for Madonna.

Here is Madonna’s performance of the song “Now I’m Following You.” It features her first dancing — and lip-syncing — with a Dick Tracy dancer, yellow coat and all. (No, it is not Warren Beatty, the star of Dick Tracy and Madonna’s boyfriend at the time.) Around the five minute-mark, Madonna strips her Dick and then is joined by six more Dicks. They take the main stage in a choreographed dance, and around the six minute-mark, the Dicks pair off and dance together, pausing only to form a chorus line that kicks high enough to show that yes, they are wearing shorts beneath those tench coats.

I’m sure the implications of a Dick-on-Dick live show weren’t lost on Madonna or most of her fans.

Considering that Dick Tracy was a big-budget summer release with a PG-13 rating, surprised me that Disney would have permitted an eroticized take on the main character. Then it occurred to me that Madonna in 1990 was wielding the fullest-ever command of her Madonna-ish powers and could basically get away with anything. She maybe didn’t even ask permission to feature a gay Dick Tracy chorus line. She’s Madonna, after all.

Either way, Dick Tracy ended up making more than $100 million, so it seems unlikely that Madonna’s method of promotion hurt the film’s box office.

Oh, 1990, you were weird.

Side note: Is it odd if Madonna, blond sexbomb, inserted into a noir universe kind of makes me think of Harley Quinn?

Pop culture, previously:

• It’s My Bat-Party, and I’ll Be a Lesbian If I Want to
• Battle of the Ambiguously Sexual Signifiers, Anime-Style
• Black Tiger and the Literal End of the Game
• Priscilla, Queen of the Tundra
• Mr. Belvedere’s Secret