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There’s absolutely no shortage of content on HBO Max. The new streaming service launched in late May with a robust library of over 600 films ranging from essential classics to modern blockbusters. Choosing which one to watch as my inaugural venture into the world of HBO Max was tough—until I saw Dick Tracy on the service.

Like all the other kids that became pop-culture-sentient in the late ’80s and early ’90s, Warren Beatty’s Dick Tracy was up there with Michael Keaton’s Batman, Kevin Costner’s generically American Robin Hood, and the Nazi-punching Rocketeer in the ranks of summer movie idols. I had to revisit Dick Tracy now that it’s—oh god, brace yourselves for a mortality check—30 years old, and I had a decidedly different takeaway now in the summer of 2020 than I did in the summer of 1990. Instead of being obsessed with the adventures of a bunch of cops (yep, you have to reckon with how pop culture really skewed how us white kids view law enforcement!), I was left breathless by Madonna’s gowns.

Not only have I not seen Dick Tracy since I was a child, I also haven’t seen it in the 15 years since I came out of the closet. So I did not know what I was in store for when Dick Tracy became my first HBO Max watch. And then I saw Madonna…

Dick Tracy - Madonna as Breathless Mahoney
Photo: HBO Max

In the grand scheme of divas, Madonna is like… upper middle-of-the-pack for me? She’s no Janet Jackson. I listen to (and love) way more of Carly Rae Jepsen. And being from the South, I claim Dolly Parton and Loretta Lynn as hometown heroes. I was not predisposed to go gaga over her in this movie, all of which illustrates how good these looks are. They’re good enough to make me pitch and write a whole article about them!

In retrospect, Dick Tracy probably represents Madonna at the peak-iest of the many, many peaks in her career. The movie came hot off the heels of her groundbreaking Like a Prayer album, and her Dick Tracy companion album I’m Breathless featured the world-changing single “Vogue.” Those two albums fueled the iconic Blond Ambition World Tour, a tour that I definitely did not see (I was 6 and very Southern Baptist) but was keenly aware of because Madonna was as omnipresent as the sun in the summer of 1990. All that is to say, when you watch Dick Tracy, you’re seeing Madonna at the height of her Madonna-ness—and she delivers.

Dick Tracy - Madonna as Breathless Mahoney
Photo: HBO Max

Madonna’s acting ability is often teased, sometimes rightfully so (you can also stream Shanghai Surprise on HBO Max). That’s not the case in Dick Tracy, which gives Madonna a part to play that was as tailor made for her as those exquisite retro gowns. She stars as Breathless Mahoney, a vampy lounge singer, a dangerous seductress, and the ultimate comic book femme fatale. But Mahoney does more than writhe on Dick Tracy’s desk and pull him into her shadow. Madonna plays Mahoney with all the tension of a clenched fist. She’s a woman caught in a bad situation with very little in the way of exits. Madonna brings a level of messy vulnerability to a character that could be no-dimensional. You can see the look of tired and annoyed resignation on her face in every scene with Al Pacino’s Big Boy Caprice.

Dick Tracy - Madonna as Breathless Mahoney
Photo: HBO Max

Mahoney turns a lot of looks in Dick Tracy, which is notable considering that nearly every other character sticks to their rigid costuming and color scheme (Dick Tracy’s canary yellow trench, Caprice’s green suspenders, etc). She has looks for performing, practicing, seducing—while Breathless Mahoney is trapped in a criminal’s nightclub, we see a whole world in her wardrobe.

Dick Tracy - Madonna as Breathless Mahoney
Photo: HBO Max

Just look at this gown she sports while paying a visit to Dick Tracy’s office! That’s Madonna strutting past the kid, who stands in for all of the gays who were completely floored by this look.

Dick Tracy - Madonna as Breathless Mahoney
Photo: HBO Max

There’s a real, “What, this old thing?” vibe to Mahoney’s energy in this film, a kind of effortless strength and unassuming confidence that, honestly, had to have been a stretch for Madonna. This is the era of Madonna getting frisky with a Black Jesus and strutting her stuff in a razor-sharp cone bra. She was strong and confident, but there was nothing unassuming about her in 1990. Madonna had the range in 1990!

Dick Tracy - Madonna as Breathless Mahoney
Photo: HBO Max

Y’know who else had the range? Academy Award-winning costume designer Milena Canonero, who scored another nod for Dick Tracy (and lost to Cyrano de Bergerac, whatever). Canonero, a frequent collaborator with Stanley Kubrick, had to come up with heightened takes on period looks for civilians, law enforcement, a menagerie of creepy mobsters, and this one night club diva. And while that’s a range of looks, Canonero actually didn’t let herself play with a wide range of colors.

As she told the Chicago Tribune in 1990, she limited herself to a color palette of 10 in order to mimic the limited printing capabilities of the source material, a 1930s comic strip. She even eliminated grays and browns from the film, which is why every character looks kinda like a crayon in a fedora. But then there’s Breathless Mahoney, who Canonero described as a “creature of the night.” Even clad in head-to-toe black sequins, she still catches your eye—even when she’s not in focus!

Dick Tracy - Madonna as Breathless Mahoney
Photo: HBO Max

That’s how stunning she is. In a movie where every character is either Warren Beatty cosplaying as a dapper banana or a who’s who of Hollywood legends covered under pounds of cartoonish latex, Mahoney is an eye-catching example of sleek and simple elegance.

No moment is wasted, either—not even a blink-and-you-miss-it look she delivers during one of the film’s many montages! Every time she’s onscreen, Canonero made sure that Mahoney was iconic.

Dick Tracy - Madonna as Breathless Mahoney
Photo: HBO Max

So if you’re going to watch Dick Tracy in the year 2020, right here and right now, then you need to do it for Madonna’s looks first and foremost. Do it for the gowns, and not for the glorification of the police. There’s one aspect of the movie that’s aged exquisitely, and it has nothing to do with Dick and everything to do with this dame.

Dick Tracy - Madonna as Breathless Mahoney

 

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