Benicio Del Toro’s Top 5 Ugliest Film Roles
18 June 2009, 4:45 PM. By Alex Alvarez
Man, Benico del Toro looks beat the hell up in character for his upcoming The Wolf Man movie. And yet, there’s something so sexy about a man who gets paid millions of dollars to is confident enough to get really dirty and ugly for a role.
And it’s not the first time Benicio’s looked busted and disgusted for a movie. Let’s take a look at his top five ugliest film roles, shall we?:
5. “Jackie Boy” in Sin City

Not only was Benicio’s character in this movie morally repugnant, he also had a weirdly pinched prosthetic nose that threw off all his other features. And his death (above) was pretty heinous, too.
4. “Dr. Gonzo” in Fear and Loathing in Las Vegas

Man, he was so weird and bloated and freaked out and awesome in this movie. As your lawyer, we advise you to watch this movie if you haven’t already.
3. “Jack Jordan” in 21 grams

God, we hated this movie. We were already bored to death of Iñárritu’s “different stories that will meet at some point in a way that is entirely too neat and pat” storytelling technique (Don’t worry, screenwriter Guillermo Arriaga. We also blame you.) and we cannot stand those brilliantly colored camera filters or whatever that makes scenes look either liked their soaked in urine or where filmed entirely underwater in a chlorinated pool. Anyway. Here’s Benicio, looking all crazy and Jesus-obsessed and gassy.
2. “Benny Dalmau” in Basquiat
He was all strung out-looking in his movie. At least his hair looked fluffy and glorious.
1. “Che” in Che
What a gross loser.
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You ever notice that Benicio always makes a face like he is smelling a fart?
I’d still do him.
awwww! c’mon! Sin City and Fear and Loathing are the only two movies where he was thoroughly repugnant.
21 Grams? I wanted to take care of him and fuck that born again creepiness out of him. He’s adorable in Basquiat if only because Dalmau was my favorite Puerto Rican b-ball player and I have a thing for basketball players.
then there’s Che. ARE YOU OUT OF YOUR MIND! you obviously didnt grow up in a left-wing household —and you must be Cuban de los de aca.
every chica izquierdista’s dream was to have her own Che. i mean, at least it was during my time. combine that with dreamboat Beni and …. OMFG, let me get a bib because am drooling.
sure, Beno’s not looking too hawt lately –he’s got to lay off the vodka shots and strippers– but if he let me smack some sense into him i’d totally bring his hotness back.
and yes am owning my enchule cronico :)
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I actually have some insane, weird attraction to him in the Dr. Gonzo/Oscar Zeta Acosta role. Except for the tub scene. That was indeed gross.
“Look, there’s two women fucking a polar bear!” “Don’t tell me these things… not now man…”