Incomplete Top 10: Hollywood's Best Onscreen Womanizers

By Caroline Kepnes Aug 08, 2007 11:48 PMTags
Ryan Phillippe, Cruel IntentionsColumbia Pictures

1. Ryan Phillippe in Cruel IntentionsWhen we meet Sebastian Valmont (Phillippe), he’s placating his shrink (Swoozie Kurtz), who has no idea he has nailed her little miss perfect daughter (Tara Reid—oh, the irony). And by the time the doc does catch on, he’s already using the situation to woo another innocent bystander girlie. Never mind that Sebastian finds true love. He’s far more fun when he’s hunting for unchartered chicks.

2. Jack Nicholson in Terms of EndearmentThe astronaut. The astronaut! If you haven’t seen this movie, then you haven’t seen Jack take Shirley Maclaine out for an upstanding, proper lunch date and tell her they are going to have to get drunk. And you haven’t seen him openly flirt with other women as she sits there. Which means you also haven’t seen him show up in her time of need and let her cry on his shoulder. We would all love him to come seduce us, even now, which is really saying something.

Columbia Pictures

4. Warren Beatty in ShampooGeorge Roundy (Beatty) can’t help it if everyone wants to sleep with him. And when everyone includes Julie Christie, Goldie Hawn, Lee Grant and Carrie Fisher, what sort of man is gonna say no? The tight pants, the endless well of charm, the hands and the attention he gives to the women are the markings of a true ace floozy. I always hope they’ll remake this movie, but who can do what Beatty does, especially in 2007, which is very much not 1975?

5. Sean William Scott in American WeddingWhat? Not American Pie? No, Wedding features Stifler at his most Stifler-esque. Stifler’s journey is proof that you don’t have to get the girl to make a list like this. You just have to try really, really hard, as in pretending to be a preppy, flower-loving sap while you hump, bump and grind the air every time she turns around. Stifler’s sexual energy is so intense that if he were to take it and apply it to finding world peace, we would probably have a Hands Across the Globe situation in minutes. Sticky hands, but still.

6. Eugene Levy and Rick Moranis in Club ParadiseLong before Steve Carell made us all laugh in The 40-Year-Old Virgin with his chest- waxing endeavor, Eugene and Rick made us cackle with their tangled torsos. They’re two guys who jet down to a new resort in the Caribbean hoping to lasso some hotties. Even when they score a bag of weed that would make most college dorms happy for weeks, they can’t land chicks. These doofuses never stop gunning for some l-o-v-i-n' and argue over their failings like an old married couple caught in a canasta battle.

Dyla Perah/Twentieth Century Fox

7. Jesse Metcalfe in John Tucker Must DieOh, so you say this movie was a disappointment. So you say Metcalfe can’t act. Well, even if he was just being himself as John Tucker, teenage Lothario, he was well cast. We all went to high school with a guy like this, a guy who leapt from one chick to the other and somehow never looked tired or disoriented or, let’s face it, ridden with STDs. Metcalfe plays Tucker as blasé, entitled and, well, toned. Sometimes it’s good when an actor doesn’t try and expand his repertoire.

8. Roger Moore in A View to a KillBlame the Duran Duran song or the fact that I was a young impressionable girl when this movie came out, but yeah, I’m a Roger girl. He’s my favorite James Bond. You can have your Pierce Brosnan and his symmetrical face. You can take Sean Connery, sexy as he is, and put him away. Moore had the devil in him. How the hell else would he have been able to wrangle Grace Jones?

Laurie Sparham/Universal Studios

9. Hugh Grant in Bridget Jones's DiaryThe bastard beds Bridg (Renée Zellweger) and the American stick figure (name not worth mentioning, argh!) and sees the light when it’s too damn late. Like all the great cads, he has the cruelest timing. And, oh, does he know how to wear a white button-down shirt. That’s pretty much what it comes down to, I think. There’s a shot of Grant when he’s just fallen out of a boat and he’s wet and the shirt is wet and he has his sunglasses on and he still has his cigarette in his mouth. Aaah. Time for a break.

Now then, who did I miss?