1. Who's That Girl (dir. James Foley, 1987)
Probably a surprising choice, given that Who's That Girl is routinely ranked amongst Madonna's most woeful efforts, and won her a second Razzie for Worst Actress in 1988. For me, though, James Foley's screwball caper - basically Bringing Up Baby updated to the contexts of 80s Yuppiedom and street culture - offers pure pop pleasure from its delightful animated credit sequence onwards, with Madonna's peroxided ex-con rifling through accents and poses as she shakes up Griffin Dunne's staid tax attorney in an attempt to bring to justice those who put her in the slammer. With a script that's blissfully silly but also surprisingly smart about American class attitudes, the movie boasts rooftop chases, hapless hoods, two Patagonian cougars, a lovely tranquil nocturnal mid-section (complete with John Mills cameo!) and the sublime Haviland Morris giving one of the great unsung comic performances of 80s cinema as a WASP princess with a secret slutty side ("Loudon, what part of Scarsdale are you in?"). Big fun.
2. A League of Their Own (dir. Penny Marshall, 1992)
As the cheeky taxi dancer finding friendship and focus on the baseball field Madonna slots right in to the terrific ensemble of Penny Marshall's loving and often very funny portrait of the women's leagues of WWII, as well as contributing the touching "This Used To Be My Playground" to the soundtrack.
3. Evita (dir. Alan Parker, 1996)
Alan Parker's long-delayed film isn't subtle, but Madonna's shrewd, intelligent performance is; she inhabits the role with an icon's understanding and delivers the score - probably Rice and Lloyd Webber's best - with a grace and elegance that's a class apart from Broadway belters.
4. Desperately Seeking Susan (dir. Susan Seidelman, 1985)
In an otherwise scathing review that indicts Leora Barish's script for stupidity and Seidelman's direction for amateurishness, Pauline Kael reserves praise for Madonna: "She moves regally, an indolent, trampy goddess [and] luxuriates in suburban materialism as if she'd discovered the pleasures of imperial Rome."
5. Dick Tracy (dir. Warren Beatty, 1990)
A timely reminder of a moment when comic book movies had some individual personality, and didn't go on forever. As Breathless, Madonna sings Sondheim and slinks through her scenes with witty, studied sultriness underpinned by a dash of melancholy. More!
Bonus: In Bed With Madonna, Bloodhounds of Broadway, Body of Evidence, (as director) W.E
Just no: The Next Best Thing, Shanghai Surprise, Swept Away