Forget Nights in Rodanthe and The Runaway Bride. I prefer my Richard Gere fix to be a little more on the naughty side.

His latest movie, Arbitrage, gives us just that. Gere's wheeling and dealing Wall Street character, Robert, is far from irreproachable. His mischievous behavior lands him in several very tight spots, and the film revolves around him trying to weasel his way out of them.

At work, Robert has been up to a little Bernie Madoff-style book cooking. He's trying to cover up a $400 million hole he created with some good old-fashioned fraud and a major deal that would see a huge bank buy up his trading firm and wash all of his missteps away. The only thing standing between him and the deal is a pesky audit (and potentially his squeaky-clean daughter, who also serves as his CFO, should she discover what he's been up to).

Beyond the office, we see that even though he appears to be happily married to his MILF-y wife (Susan Sarandon), he's got a much younger piece on the side -- a temperamental artist played by Laetitia Casta ('90s model. Remember her?) When he tries to whisk the mistress off on an overnight getaway, things go horribly wrong, and Robert has a whole new level of mess to clean up. Enter an overzealous detective (Tim Roth) who hates seeing rich Wall Street guys get away with everything, and things turn from bad to worse for Robert.

Will he finagle his way out of his messes? Should he? Part of Gere's magic is that even when he's playing not-so-good guys, you can't help but root for him. He's just so darn smooth. And handsome. And charming.

I could go on and on, but instead, I've compiled a list to prove my point. Here's a rundown of my top five favorite Gere bad boy roles.

1. American Gigolo. Narcissistic Julian knows he's got it going on, and he doesn't mind making the ladies pay for what he's got to offer. After all, cocaine and cars don't pay for themselves! Gere is so perfect in this iconic role, it's hard to believe he was a last-minute replacement for John Travolta.

2. Pretty Woman. Sure, he ultimately comes off as a pretty decent guy who whisks Julia Roberts off the streets. But he's picking hookers up off the streets. Not exactly Boy Scout material. And really, what kind of rich guy picks hookers up off the streets? Didn't they have classy escort services in the early '90s?

3. Chicago. Slick lawyer Billy Flynn certainly knows how to work the system and manipulate public favor. With his perfectly coiffed hair and sharp three-piece suits, it's easy to see how Billy could tap dance his way out of anything -- for both himself and his clients.

4. The Cotton Club. With a little mustache like that, you know Dixie has got to be up to some kind of no good. The struggling jazz musician makes a deal with the devil -- well, the Mob, but close enough -- in order to advance his career. Naturally, complications ensue. 5. Primal Fear. Gere sure looks good in a courtroom, doesn't he? This time around, he plays a publicity-hungry lawyer named Martin who chases high-profile cases and wealthy clients. As the movie progresses, you see a softer side emerge as starts to believe in his pro-bono altar boy client. Whether that faith is deserved or not is an entirely other question. Is the player being played?

Arbitrage Movie Poster
Based on 35 critics

As he approaches his 60th birthday, New York hedge-fund magnate Robert Miller (Richard Gere) is the picture... Read More

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