Brad Pitt's Best & Worst Movie Roles

The Best

10. <a href='http://movies.aol.com/movie/the-assassination-of-jesse-james-by-the-coward-robert-ford/26180/main'target='_blank'>'The Assassination of Jesse James'</a> (2007)

<b>Who He Plays:</b> Legendary outlaw Jesse James<br><b>Why It Ranks:</b> His moody portrayal of James in this dreamy Western has won Pitt a Best Actor award at the Venice Film Festival and the best acting reviews of his career. He goes deep and dark -- and we don't just mean his hair color.

The Best

9. <a href='http://movies.aol.com/movie/true-romance/8234/main'target='_blank'>'True Romance'</a> (1993)

<b>Who He Plays:</b> Scene-stealing stoner Floyd<br><b>Why It Ranks:</b> Despite having less than 10 minutes of screen time and never leaving the couch, Pitt's Floyd is both pivotal to the story (he tells the mafia where the climactic drug deal is going down) and hilarious ("Get some beer ... and some cleaning products!").

The Best

8. <a href='http://movies.aol.com/movie/a-river-runs-through-it/7290/main'target='_blank'>'A River Runs Through It'</a> (1992)

<b>Who He Plays:</b> He's Paul Maclean, hard-living younger brother to narrator Norman (<font color="#1C5BB0"><a href="http://movies.aol.com/celebrity/craig-sheffer/111090/main"target="_blank">Craig Sheffer</a></font>).<br><b>Why It Ranks:</b> Sheffer's the lead, but it's Pitt who blazes across the screen, playing a rebel who flings himself into life (and fly-fishing) with the recklessness of the brilliant and the doomed.

The Best

7. <a href='http://movies.aol.com/movie/thelma-and-louise/4611/main'target='_blank'>'Thelma & Louise'</a> (1991)

<b>Who He Plays:</b> A cute drifter who gives Thelma (<font color="#1C5BB0"><a href="http://movies.aol.com/celebrity/geena-davis/17342/main"target="_blank">Geena Davis</a></font>) the best sex of her life -- then robs her blind<br><b>Why It Ranks:</b> Pitt's breakout role isn't memorable just for his shirtless scene. The actor radiates charm, wit and ... Oh, who are we kidding? It's all about the shirtless scene. (Lawdy!)

The Best

6. <a href='http://movies.aol.com/search/movieanddvdresults?query=Ocean's'target='_blank'>The 'Ocean's' Trilogy</a>

<b>Who He Plays:</b> Rusty Ryan's "The Pro" in Danny Ocean's (<font color="#1C5BB0"><a href="http://movies.aol.com/celebrity/george-clooney/13722/main"target="_blank">George Clooney</a></font>) gang of thieves.<br><b>Why It Ranks:</b> Pitt's the embodiment of these heist films: He's quick, clever and crazy good-looking, with crack comic timing and a taste for the ridiculous. (Could Clooney rock that Ted Nugent suit? We think not.)

The Best

5. <a href='http://movies.aol.com/movie/babel-2006/25148/main'target='_blank'>'Babel'</a> (2006)

<b>Who He Plays:</b> A tourist whose wife (<font color="#1C5BB0"><a href="http://movies.aol.com/celebrity/cate-blanchett/215038/main"target="_blank">Cate Blanchett</a></font>) suffers a gunshot wound<br><b>Why It Ranks:</b> It's not difficult to be severely affected (or depressed) by an <font color="#1C5BB0"><a href="http://movies.aol.com/celebrity/alejandro-gonzalez-inarritu/297411/main"target="_blank">Alejandro Gonz&#225;lez I&#241;&#225;rritu</a></font> drama, but Pitt's wrenching turn only intensifies it. The scene where he fights back tears on the phone is his most powerful moment to date.

The Best

4. <a href='http://movies.aol.com/movie/snatch/8757/main'target='_blank'>'Snatch'</a> (2000)

<b>Who He Plays:</b> Gypsy brawler Mickey O'Neil, pronounced "Mkayonee"<br><b>Why It Ranks: </b><font color="#1C5BB0"><a href="http://movies.aol.com/celebrity/guy-ritchie/242801/main"target="_blank">Guy Ritchie</a></font>'s follow-up to <font color="#1C5BB0"><a href="http://movies.aol.com/movie/lock-stock-and-two-smoking-barrels/5477/main"target="_blank">'Lock Stock'</a></font> is just as deliciously perverse, especially given the addition of Pitt's animalistic, bare-knuckle bruiser, whose completely incoherent gypsy tongue offsets his costars' mostly incoherent English.

The Best

3. <a href='http://movies.aol.com/movie/twelve-monkeys/1833/main'target='_blank'>'12 Monkeys'</a> (1995)

<b>Who He Plays:</b> Jeffrey Goines, a mental patient who may hold the key to helping time traveler <font color="#1C5BB0"><a href="http://movies.aol.com/celebrity/bruce-willis/76618/main"target="_blank">Bruce Willis</a></font> prevent the outbreak of a deadly virus<br><b>Why It Ranks:</b> Pitt's role in the twisty thriller earned him his only Oscar nomination to date (for Supporting Actor), proving once again that the Academy loves crazy.

The Best

2. <a href='http://movies.aol.com/movie/fight-club/6690/main'target='_blank'>'Fight Club'</a> (1999)

<b>Who He Plays:</b> The first rule about Tyler Durden is you don't talk about Tyler Durden.<br><b>Why It Ranks:</b> Fans of the cult novel once wondered if Pitt was too pretty for the role, but no more: The volatile Pitt IS Tyler Durden, a revolutionary with fists and soap, insanely charismatic and just ... insane.

The Best

1. <a href='http://movies.aol.com/movie/seven/1538/main'target='_blank'>'Seven'</a> (1995)

<b>Who He Plays:</b> David Mills, a brash young detective who teams with <font color="#1C5BB0"><a href="http://movies.aol.com/celebrity/morgan-freeman/90514/main"target="_blank">Morgan Freeman</a></font> to investigate a series of grisly murders based on the seven deadly sins<br><b>Why It Ranks:</b> It's one of the most shocking thrillers ever made, and Pitt's final, visceral scene ("What's in the box?!") will haunt you for days.

The Worst

5. <a href='http://movies.aol.com/movie/seven-years-in-tibet/4935/main'target='_blank'>'Seven Years in Tibet'</a> (1997)

<b>Who He Plays:</b> German mountaineer Heinrich Harrer, who tutored the young Dalai Lama from 1944-51<br><b>Why It Ranks:</b> Pitt's German accent was simply <i>furchtbar</i> (that's German for "awful"). Plus, Pitt and co-star <font color="#1C5BB0"><a href="http://movies.aol.com/celebrity/david-thewlis/70493/main"target="_blank">David Thewlis</a></font> were banned from China for life as a result of the movie's pro-Tibetan themes.

The Worst

4. <a href='http://movies.aol.com/movie/the-devils-own/3737/main'target='_blank'>'The Devil's Own'</a> (1997)

<b>Who He Plays:</b> IRA terrorist hiding in the basement of an NYC cop (<font color="#1C5BB0"><a href="http://movies.aol.com/celebrity/harrison-ford/24238/main"target="_blank">Harrison Ford</a></font>)<br><b>Why It Ranks:</b> For all its pedigree -- Oscar-nominated director <font color="#1C5BB0"><a href="http://movies.aol.com/celebrity/alan-j-pakula/105408/main"target="_blank">Alan J. Pakula</a></font>, A-list stars Pitt and Ford -- this pseudo-political thriller doesn't spark. (It doesn't help that Pitt's Irish accent is about as authentic as the Lucky Charms leprechaun.)

The Worst

3. <a href='http://movies.aol.com/movie/meet-joe-black/4559/main'target='_blank'>'Meet Joe Black'</a> (1998)

<b>Who He Plays:</b> A surprisingly smitten Death<br><b>Why It Ranks:</b> The Grim Reaper looks like Brad Pitt, so does it surprise anyone that the flick is unintentionally silly at times? And at almost three hours long, the best we can say of 'Black' is that it almost makes us wish for the sweet embrace of Brad ... er, death.

The Worst

2. <a href='http://movies.aol.com/movie/cool-world/6840/main'target='_blank'>'Cool World'</a> (1992)

<b>Who He Plays:</b> A detective sucked into a world where humans coexist with cartoon characters<br><b>Why It Ranks:</b> "Sucked" being the operative word. This <font color="#1C5BB0"><a href="http://movies.aol.com/movie/who-framed-roger-rabbit/1039070/main"target="_blank">'Roger Rabbit'</a></font> wannabe (ouch) has about as much charm to it as a stick figure. It also required Pitt to wear a bright purple suit (no green mask, though).

The Worst

1. <a href='http://movies.aol.com/movie/the-mexican/9154/main'target='_blank'>'The Mexican'</a> (2001)

<b>Who He Plays:</b> Lovable loser at odds with the mob AND his girlfriend (<font color="#1C5BB0"><a href="http://movies.aol.com/celebrity/julia-roberts/60634/main"target="_blank">Julia Roberts</a></font>)<br><b>Why It Ranks:</b> Forget the fact that the film's called 'The Mexican' and stars three white folks (<font color="#1C5BB0"><a href="http://movies.aol.com/celebrity/james-gandolfini/25753/main"target="_blank">James Gandolfini</a></font> also appears). This clunker was the long-awaited Brad-Julia collaboration, and wound up '01's most disappointing film.