Sean Penn’s best costumes

Niels Ruëll
© Agenda Magazine
21/03/2012


1. Fast Times at Ridgemont High (1982)
One of the better comedies about high school kids hungry for sex, fun, and music. Screenwriter Cameron Crowe wrote from personal experience. Disguise: Long blond hair, an oversized T-shirt, or an unbuttoned shirt that shows his burly chest. But what really completes Penn’s surfer dude is the hazy look with which he claims to be off the dope.

2. We’re No Angels (1989)
Neil Jordan directing a script by David Mamet about two escaped convicts who hide in a church and are mistaken for priests. Disguise: Like Robert De Niro, Penn dons a black cassock and biretta. A white chasuble and a Bible he always carries with him complete the outfit.

3. Carlito’s Way (1993)
A classic by Brian De Palma. After his release from prison, a drug dealer with Puerto Rican roots tries to stay on the straight and narrow, but fails miserably. Disguise: What turns an unrecognisable Penn into the disgustingly sleazy lawyer David Kleinfeld? The glasses help, but his hairdo steals the show: a slick perm in the style of Lionel Richie.

4. Sweet and Lowdown (1999)
Woody Allen celebrates his love of jazz in this pseudo-documentary portrait of Emmet Ray, a jazz virtuoso obsessed with Django Reinhardt who gets himself into all kinds of trouble. Disguise: Penn goes Django. The guitar is like an extension of his arm, and the cigarette of his lips. But the little moustache outperforms everything and everybody else.

5. I Am Sam (2001)
An awful film about a mentally handicapped man fighting for custody of his seven-year-old daughter who is already smarter than him. Disguise: Penn presents the man with a low IQ as someone who can’t keep his hands still and walks around with his mouth open so far you could fit a tennis ball in it. Good enough for an Oscar nomination, apparently.

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