In Honor of W.E., Madonna's 5 Best Moments on the Big Screen

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Madonna's much-maligned W.E. opens in limited release in New York and L.A. this week, and I thought we'd wipe the taste of Venetian backlash and hydrangea topnotes out of our mouths and remember five occasions when Lourdes's mother kicked ass in films. Because she did, people. Let's strap on our bangles, writhe in our fishnets, and point our cone bras back at Madonna's sunnier moments at the cineplex.

5. Breathless Mahoney's coquettish insecurities in Dick Tracy

While Madonna is too voracious and self-conscious a superstar to be a Betty Boop-type coquette, she makes a lot of her cutesy dialogue believable in Dick Tracy, the '90 comic-book caper that holds up surprisingly well. If her nightclub rendition of the Oscar-winning tune "Sooner or Later" doesn't stop you in your tracks, you'll emit a gentle guffaw here when she coos, "I know how you feel. You don't know if you want to hit me or kiss me. I get that a lot." Do I detect a strand of Grace Kelly's accent in that voice?

4. Susan's woozy wiles in Desperately Seeking Susan

If superstardom is about timing as much as talent, then Madonna cashed in at just the right moment with her debut performance in Desperately Seeking Susan. As the titular dance-hall urchin who ends up trading places with a bored housewife (Rosanna Arquette), Madonna landed the chance to play and promote herself: a cheeky, brash, intermittently straightforward man-killer with undeniable charisma. Watch here as she befuddles Mark Blum, who's not even clever enough to realize the music playing is Madonna's own "Into the Groove."

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3. The grit of Dangerous Game

Madonna once said of her starring role in Dangerous Game, the '93 Abel Ferrara film that was released (barely) on her own Maverick imprint, "Even though it's a shit movie and I hate it, I am good in it." I have to agree: She's both chillier and more vulnerable here than in any of her earlier films, and it's impossible to look away from her as she spars with Harvey Keitel. Ironically, she's pretty damn effective when playing an actress.

2. The tender side of A League of Their Own's "All the Way" Mae

The denial ends here: You can have your Evitas and Dick Tracys, but the single best Madonna movie (with a narrative) is A League of Their Own. As "All the Way" Mae Mordabito, Madonna is a naughty, yet emotional powerhouse on the Rockford Peaches, a WWII-era women's baseball team. Here, she helps a teammate learn to read with the aid of some steamy literature. While working entirely in the company of women, Madonna seems perfectly at ease as an actress -- she even outshines her Oscar-winning teammate Geena Davis.

1. The candor of Truth or Dare

There's no replacing or topping Truth or Dare, the documentary that chronicles Madonna during her very best tour and at her most staggering popularity. The black-and-white cinematography somehow feels unpretentious here, perhaps because it's offset by such fulgent, Technicolor concert sequences. The single best moment, in my estimation, is the actual "Truth or Dare" game where backup singer Donna DeLory asks Madonna to name the love of her life. Like a material girl who lives to tell, Madonna follows suit, and it's a heartbreaking and unforgettable reveal.

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  • BWags says:

    You could actually come up with five?

  • SunnydaZe says:

    I am fond of this>
    Sure, her acting is a bit stiff but she is an imposing figure and proves at the end she doesn't take herself too seriously. My favorite moment is when "the driver" is on the phone and she is making faces and mocking him from the back seat just like a child.

  • Andrea says:

    and EVITA where is it???

  • Mel says:

    I may have just breathlessly clicked on this story to see what moment you selected from "A League of Their Own". Oh, but how could anyone choose?

  • Alonso Duralde says:

    I think her best work is in her most obscure movie -- if you can ever track down a copy of "Bloodhounds of Broadway," you'll be shocked at how good she is in it.

  • NP says:

    Her best moment is in Alison Anders' segment of _Four Rooms_, "The Missing Ingredient." The quick scene with her and Alicia Witt and Tim Roth in the lobby is gold. I love it.
    Side note: please please please do a "Bad Movies We Love" feature on _Four Rooms_.

  • Kerrylyn says:

    Hello, Evita! Major film. Madonna was grande.

  • bedtimeboy says:

    She's had her up and downs, but she can definitely act.
    Susan, Eva or Breathless are unforgettable.

  • Louis Virtel says:

    That's one Madonna movie I've not seen. I actually had no idea it was rare, so now I feel a little better about it.

  • Maya says:

    What? No Evita?

  • lakawak says:

    You should all check her out in this little movie that no one has seen which makes it SOOOO much better than the others. And it makes me SO much better a movie watcher because I HAVE seen it!

  • Charles says:

    Evita should have been an easy No. 1 for Madonna: no dialogue, all singing.

  • Cheri Gayles says:

    Does anybody remember Who's That Girl, her really clumsy remake of Bringing Up Baby? Admittedly, her acting skills weren't on display, but there were some salvageable moments and I really liked Griffin Dunne in this one (for a change he was stuffy). Her songs on the soundtrack, though, are good and a time capsule of where she was musically during that period. Question: why isn't WTG on DVD? I hate to admit it , but it's been a long time since I've seen it and, well...

  • "Does anybody remember Who's That Girl, her really clumsy remake of Bringing Up Baby?"
    Do we ever:

  • paul garcia says:

    i think she did a good job in Girl 6 and Swept Away,you just have to have patience w who she is as an icon and actress.

  • Goleft says:

    OK, i admit it, I am really old. I saw Desperately Seeking Susan as a teenager! Nevertheless just as Enemen played himself in nine mile, Madonna fitted perfectly into this music video like film. She may never be a great actor, so why she just doesnt play characters close to her type and be admired for who she is and what she has done for music culture is beyond me.

  • Hey, I thought In a league was a pretty good acting role. Sure she was the alpha woman on the team, and got to be gross and pretty at the same time (mimicking life) but so what if it works. I liked it anyway.

  • Marina72 says:

    Agree with these choices, and I also liked Madonna in Evita and Bloodhounds of Broadway (and I'll admit Shanghai Surprise is a guilty pleasure.)