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TODAY contributor
updated 9/19/2011 4:32:58 PM ET 2011-09-19T20:32:58

If you built a movie star from scratch, he would probably possess these qualities: traffic-stopping looks, charisma, wit, character, and probably most important, the savvy to get to the top of the Hollywood heap and remain there.

Somehow, Brad Pitt figured out the formula. But it isn’t that simple. He also seems to have pursued a career with a dismissive shrug toward conventional wisdom. Take a gander at his credits and notice that, although there are plenty of times when his name stood atop the marquee (“Legends of the Fall,” “Meet Joe Black,” “Seven Years in Tibet”), many of his most memorable roles were in supporting or ensemble roles ("Thelma & Louise," “Twelve Monkeys,” the “Ocean’s Eleven” series, “Inglourious Basterds”).

Also, he has defied the norm further with forays into art-house fare like “Babel” or the recent Terrence Malick film, “The Tree of Life.” And he does all of that while in a relationship with Angelina Jolie that couldn’t be more high profile if they adopted a Kardashian.

This week, Pitt tosses another curve with “Moneyball,” the story of Oakland Athletics general manager Billy Beane, who devised a new way of evaluating talent and building a baseball franchise that upset the establishment’s way of thinking.

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Sort of like the way Brad Pitt approaches acting.

“Looking at Pitt's career to date, I'd say he's done a remarkable job of alternating roles that keep him on the A-plus list as a leading man with interesting, challenging parts in quirkier and smaller films,” noted film critic Richard Roeper of the Chicago Sun-Times and the ReelZ channel. “I'm not saying he's Paul Newman because there was only one Paul Newman. But there's a similarity between the two in that they refused to coast on their looks and garnered more respect as they got a little bit older and their faces had more character.


Slideshow: Brad Pitt's rise to stardom (on this page)

“One of the things I respect about Pitt is he never phones it in, even when he's doing light lifting in an ‘Oceans’ movie. You can tell he's always trying to add something interesting or three-dimensional to even the most mainstream characters he's played. I don't know if he's broken the mold of the typical Hollywood leading man's career, but I think he's made consistently strong choices. Even if the films don't quite work, he's never dull.”

Pitt has managed quite well to overcome the debilitating physical curse of being strikingly handsome. Yes, that’s an advantage to some degree in singles bars, in the business world and in modeling. And yes, even in motion pictures. But it can also work against a gifted actor, who can become lionized for his looks while at the same time denigrated for being a pretty boy.

Yet all the images on movie posters, as well as those on the covers of glossy supermarket tabloids featuring Pitt standing alongside his equally famous squeeze while a screaming headline spells doom for their union, remarkably hasn’t seemed to dampen his career momentum one iota.

Story: Jonah Hill wanted to live in 'Simpsons' town

“Rather than chafing against his good looks in the style of Johnny Depp,” explained movie critic Elizabeth Weitzman of the New York Daily News, “he’s embraced them to interesting effect. He does occasionally subvert expectations, by showing us the limitations of physical beauty in ‘The Curious Case of Benjamin Button,’ or reminding us that a pretty face is no guarantee of a strong mind, as in ‘Burn After Reading.’

“Overall, his most interesting performances have been the ones in which he disregards audience assumptions — like his hilariously unintelligible comic turn as an Irish fighter in ‘Snatch.’ However, he’s perfectly comfortable playing the hero, in a way Depp is not, and even his antiheroes are undeniably cool. Tyler Durden (“Fight Club”) could reasonably be called a cult icon.”

Actors like to use the tightrope analogy, which may have been popularized with Al Pacino in his early stage days. But historically there has always been a semblance of the same idea in every performer’s philosophy: You have to take great risks to get great rewards.

Pitt certainly has adhered to this in his professional life. Yet the personal side, in many ways, might be even more of a gamble. When two extremely successful Hollywood stars pair up, intense strain often ensues. That can result from one spouse having more success than the other (see: Reese Witherspoon and Ryan Phillippe, now divorced) or the celebrity persona rising while the star fades (Tom Cruise and Katie Holmes).

Oddly, Pitt seems to have glided through all that. Even a recent minor blip on the gossip meter involving a comment he made in an interview about his previous marriage to Jennifer Aniston — which he was quick to clarify — was quickly forgotten.

Pitt says he learned lesson from Aniston fallout

There will continue to be a public fascination with Pitt-Jolie as long as it exists, but it also seems obvious that if Pitt has weathered it this long, he’s probably immune to the scrutiny.

“Unfortunately, Pitt is a prime example of someone whose celebrity has very nearly eclipsed his career,” Weitzman said. “He’s responsible to some degree — 2005’s infamous ‘Domestic Bliss’ spread in ‘W’ comes to mind — but it’s hard to imagine he appreciates the endless tabloid obsession with his personal life.

“It would be nice to think that eventually people will stop caring what he does at home, and focus more on his efforts onscreen. But right now that seems about as likely as the notion of aging backwards.”

Regardless of what People magazine and the National Enquirer have to say about him and Angelina, fans tend to keep his career flourishing by purchasing tickets. According to the site boxofficemojo.com, Pitt’s 30 films have grossed over $2 billion domestically.

(Interestingly enough, Jolie’s 28 films have grossed almost $1.6 billion domestically, and her biggest box office total came with “Mr. and Mrs. Smith” at over $186 million domestically, which of course also starred Pitt, and which also represented his highest total to date.)

“That puts him in a particular stratosphere,” noted Brandon Gray of boxofficemojo.com. “It isn’t the highest gross total, but many actors above him in total grosses have their tallies padded by supporting parts or parts in animated movies. Brad has done a couple of animated films, but he’s typically a leading man.”

Gray went on to say that Pitt’s box-office performances overall have been even stronger internationally. “Some of his movies that haven’t always fared well domestically have done well overseas, even before the foreign market became so explosive,” he said. “A Brad Pitt vehicle could do twice as much overseas typically, in the '90s.”

Andrew Stewart, who covers box office for Variety, noted that Pitt belongs among a group of actors who had their heydays in the 1990s. Yet in Pitt’s case, he still attracts moviegoers. “You look at a star like Tom Cruise or Mel Gibson, you certainly can’t say the same about them as you can about Brad Pitt,” he said.

And Stewart explained that there is good reason for that, which goes back to Pitt’s eclectic tastes in projects. “He’s very smart in the types of pictures he does,” he said. “He doesn’t do a lot of big tentpole films. Not a lot of screwy comedies that could in any way hurt his brand. He works with auteurs and makes films that both adult audiences and young audiences want to see. ‘Inglourious Basterds’ is a prime example.”

“Moneyball” might be an especially hard sell. Generally speaking, baseball movies have had limited appeal. “This is not a traditional baseball movie, either, nor does it have a romantic angle like ‘Jerry Maguire’ had,” Gray said. “So I don’t think this is going to sell like a Brad Pitt movie in the sense that people have flocked to Brad Pitt movies in the past. But certainly his presence should help the movie.”

Naturally, Hollywood folks will be fixated on the bottom line. For Pitt, however, the bottom line is something he continually dances along en route to new and creatively fulfilling territory.

Said the Daily News’ Weitzman: “He always seems determined to earn not just easy admiration but our respect, with an added layer of self-awareness and gravitas.”

Do you take Brad Pitt seriously as an actor, or is he just a good-looking guy who got lucky? Discuss on Facebook.

Michael Ventre is a regular contributor to TODAY.com. Follow him on Twitter.

© 2013 NBCNews.com  Reprints

Video: Watch the 'Moneyball' trailer

Photos: Actor, activist, dad: Brad Pitt's roles through the decades

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  1. WWII tank drama

    From left, actor Logan Lerman, Brad Pitt and Jon Bernthal pose in front of a Sherman Tank during a photocall for the film 'Fury' at Bovington Tank Museum on August 28, 2014 in Bovington, England. Set at the very end of World War II, in April 1945 as the Allies make their final push in the European Theater, the film follows a battle-hardened army sergeant who commands a Sherman tank and her five-man crew on a deadly mission behind enemy lines. (Chris Jackson / Getty Images) Back to slideshow navigation
  2. Battle ready

    Pitt goes to war in the upcoming film "Fury," a film also starring Logan Lerman, Scott Eastwood, Michael Pena and Shia LaBeouf. (Columbia Pictures) Back to slideshow navigation
  3. Activists

    UN Special Envoy and actress Angelina Jolie and Brad Pitt attend the Global Summit to End Sexual Violence in Conflict at ExCel on June 13, 2014 in London, England. (Eamonn M. Mccormack / Getty Images) Back to slideshow navigation
  4. Supporting his lady

    Actress Angelina Jolie and Brad Pitt arrive at the World premiere of "Maleficent" at the El Capitan Theatre on May 28, 2014 in Hollywood, California. (Frazer Harrison / Getty Images) Back to slideshow navigation
  5. Black tie event

    Brad Pitt and Angelina Jolie attend the Oscars held at Hollywood & Highland Center on March 2, 2014. (Jason Merritt / Getty Images) Back to slideshow navigation
  6. Saving grace

    Brad Pitt appears in 2013's "12 Years a Slave" as a home builder from Canada, and learns some disturbing information about one of the slaves on the plantation where he's working. The film is based on a true account of Solomon Northup, a free man who was kidnapped into slavery. (Fox Searchlight) Back to slideshow navigation
  7. Man of the 'Years'

    Pitt's new film "12 Years a Slave" doesn't have a starring role for him, but his small part is pivotal in the action. Here, the actor arrives at the film's premiere at the Toronto International Film Festival on Sept. 6, 2013. (Chris Pizzello / AP) Back to slideshow navigation
  8. Swarming dead

    Pitt plays a former United Nations employee whose family is swept up in an abrupt outbreak of zombies in "World War Z." (Jaap Buitendijk / AP) Back to slideshow navigation
  9. On the move

    Toting as many as six children along at a time, Jolie and Pitt can't help but cause a scene, as they arrive with Knox, Vivienne and Pax at Tokyo's Haneda International airport on July 28, 2013. Pitt was in town to promote "World War Z." (Issei Kato / Reuters) Back to slideshow navigation
  10. Family bonding

    Pitt and Jolie bring two of their six children, Maddox and Pax, to the "World War Z" premiere in London on June 2, 2013. (Stuart C. Wilson / Getty Images) Back to slideshow navigation
  11. Power couple

    Jolie and Pitt stepped out on the red carpet at the "World War Z" premiere in Berlin on June 4, 2013. The expensive zombie film went through a laborious production process, but brought in over $500 million in box office worldwide. (Sean Gallup / Getty Images) Back to slideshow navigation
  12. Gotta wear shades

    Pitt poses on the red carpet ahead of the screening of his film "Killing Them Softly," at the 65th Cannes Film Festival in France, on May 22, 2012. (Eric Gaillard / Reuters) Back to slideshow navigation
  13. At gunpoint

    In "Killing Them Softly," Pitt plays a professional enforcer investigating a robbery of a mob-protected poker game. (Melinda Sue Gordon / Cogan's Productions) Back to slideshow navigation
  14. Helping out

    Pitt poses for a photo with a family who's been helped by the Make It Right foundation in the Lower 9th Ward in New Orleans, on March 9, 2012. Make It Right works to build sustainable homes and buildings. (Donald Traill / AP) Back to slideshow navigation
  15. Super couple

    Pitt and partner Angelina Jolie arrive at the 18th Annual Screen Actors Guild Awards at The Shrine Auditorium on Jan. 29, 2012 in Los Angeles. (Jason Merritt / Getty Images) Back to slideshow navigation
  16. Golden couple

    Jolie and Pitt arrive at the Golden Globe Awards on Jan. 15, 2012, in Beverly Hills, Calif. Pitt holds a cane due to a leg injury sustained after falling on a ski slope. Pitt was nominated for "Moneyball" and Jolie for "In the Land of Blood and Honey," though neither won. (Jason Merritt / Getty Images) Back to slideshow navigation
  17. White House visit

    Pitt and Jolie (not seen) visit President Barack Obama on Jan. 11, 2012 in the Oval Office in Washington, DC. to discuss humanitarian work. (Brendan Smialowski / Getty Images) Back to slideshow navigation
  18. 'Moneyball'

    Pitt plays Oakland A's general manager Billy Beane in "Moneyball," based on Michael Lewis' non-fiction book. Jonah Hill co-stars. (Melinda Sue Gordon / Columbia Pictures) Back to slideshow navigation
  19. Brad Pitt and young baseball players from an area affected by the March 11, 2011 earthquake and tsunami disaster, pose for a photo during the Japan premiere of Pitt's latest film "Moneyball' in Tokyo on Nov. 9, 2011. (Kazuhiro Nogi / AFP - Getty Images) Back to slideshow navigation
  20. Family affair

    Accompanied by their six children, Pitt and Jolie arrive at Haneda Airport in Japan on Nov. 8, 2011. Pitt was there for the Japan premiere of his film, 'Moneyball'. (Toru Yamanaka / AFP - Getty Images) Back to slideshow navigation
  21. Red-carpet ready

    Pitt and Jolie leave the festival palace after the screening of the film "The Tree of Life" at the 64th Cannes Film Festival on Monday, May 16, 2011 (Yves Herman / Reuters) Back to slideshow navigation
  22. 'The Tree of Life'

    "The Tree of Life" is a period piece that centers around three boys in the 1950s, whose parents are played by Pitt, right, and Jessica Chastain, left. The film received the Palme d'Or, the top prize, at the 2011 Cannes Film Festival. (Cannes Film Festival / Ho / EPA) Back to slideshow navigation
  23. Movie talk

    Pitt, left, and co-star Jessica Chastain attend a press conference for "The Tree of Life" on Monday, May 16, 2011 at the Cannes Film Festival. (Lionel Cironneau / AP) Back to slideshow navigation
  24. Family outing

    Jolie and Pitt take all their children (from left), Vivienne, Shiloh, Knox, Zahara, Pax and Maddox out for a walk to pick up candy in New Orleans in March 2011. (splashnews.com) Back to slideshow navigation
  25. Pitt's proxy

    Actor Will Ferrell, left, and actress Tina Fey, right, flank a cardboard cut-out of Pitt at the "Megamind" panel during Comic-Con 2010 at San Diego Convention Center on July 22, 2010 in San Diego, Calif. (John Shearer / Getty Images) Back to slideshow navigation
  26. Goodwill ambassadors

    Jolie and Pitt visit refugees in the Bosnian village of Medjedja, 43 miles east of Sarajevo, on Monday, April 5, 2010. Jolie and Pitt visited Bosnia to spotlight the plight of 117,000 people who have not been able to return to their homes since the end of the Bosnian war. (Amel Emric / AP) Back to slideshow navigation
  27. Watching mommy work

    Shiloh Jolie-Pitt, left, Pitt, and Zahara Jolie-Pitt, right, visit the "Salt" film set at Pier 66 in New York on Dec. 29, 2009. (Ray Tamarra / Getty Images Contributor) Back to slideshow navigation
  28. Yes, he Cannes

    Pitt promotes "Inglourious Basterds" at the 62nd edition of the Cannes Film Festival in Cannes, France, on May 20, 2009. Pitt told TODAY's Ann Curry, "In true Tarantino style, it's outrageous." (Guillaume Horcajuelo / EPA) Back to slideshow navigation
  29. Lucky 'Basterd'

    Eli Roth, left, and Pitt are shown in a scene from 2009's "Inglourious Basterds." Quentin Tarantino directed this film about a group of Jewish American soldiers during World War II who decide to fight back by scalping and murdering Nazis. The director told the Daily Beast, "I enjoy the war-mission subgenre but I want to forward it, make it bigger, broader, more artistic." (Francois Duhamel / AP) Back to slideshow navigation
  30. Man of the people

    Pitt, with Speaker of the House Nancy Pelosi, left, and House Democratic Whip James Clyburn, right, speaks to the news media in the U.S. Capitol after a meeting to promote New Orleans reconstruction in Washington on March 5, 2009. The Obama administration announced it would commit another $438 million toward redeveloping Gulf Coast communities still rebuilding from Hurricane Katrina in 2005. (Shawn Thew / EPA) Back to slideshow navigation
  31. 'Button-ed' up

    Pitt and partner Angelina Jolie arrive at the premiere of "The Curious Case of Benjamin Button" in Paris on Thursday, Jan. 22, 2009. "Button" was nominated for 13 Oscars, but won just three, for makeup, art direction and visual effects. (Thibault Camus / AP) Back to slideshow navigation
  32. Out with the kids

    Pitt and Jolie with their children walk through Narita International Airport in Narita, east of Tokyo, Japan, on Tuesday, Jan. 27, 2009. They arrived in Tokyo for the Japan premiere of "The Curious Case of Benjamin Button." Pitt and Jolie have six children: Maddox, Zahara, Pax, Shiloh, Knox and Vivienne. (Haruka Nakagawa / AP) Back to slideshow navigation
  33. On the 'Case'

    In 2008's "The Curious Case of Benjamin Button," Pitt starred as a man who is born old and then ages backward. Pitt told Rolling Stone, "I find 'Benjamin' is about those universal things we all share -- that 95 percent that makes us all the same, wherever we are in the world. Our loves, our hopes, but also the loss that we all walk around with and hide very well, and the ultimate notion that we're all expendable." (Paramount Pictures) Back to slideshow navigation
  34. 'Burn,' baby, burn

    In 2008's Coen brothers' comedy, "Burn After Reading," Pitt co-starred as a gym employee who stumbles upon the secret memoir of a CIA agent, played by John Malkovich. He and his co-worker, played by Frances McDormand, decide to blackmail Malkovich, with unfortunate results. "It’s much more fun to play the guys who make the wrong choices, have limited experience, and make the wrong presumptions," Pitt told Spoutblog.com. (Focus Features) Back to slideshow navigation
  35. Welcome the twins

    On July 12, 2008, Jolie gave birth to Knox Leon and Vivienne Marcheline at the Lenval hospital in Nice, France. The first pictures of the babies sold for $14 million to People magazine and Hello! The money went to the Jolie-Pitt foundation. (People) Back to slideshow navigation
  36. Expecting and red carpet ready

    Pitt and Jolie promoted Jolie's film, "Kung Fu Panda," at the 61st Cannes Film Festival on May 15, 2008. At the time, Jolie was pregnant with her twins Knox and Vivienne. (Matt Sayles / AP) Back to slideshow navigation
  37. Putting his money where his mouth is

    Pitt shows off Kellogg Park, a technologically advanced playground in the Lower 9th Ward that uses solar energy to run its electronic wireless game system in New Orleans on Dec. 1, 2008. The playground sits among homes being built through Pitt's Make It Right Foundation. (Alex Brandon / AP) Back to slideshow navigation
  38. That James boy

    Pitt starred as Jessie James in 2007's "The Assassination of Jesse James by the Coward Robert Ford." Robert Ford, played by Casey Affleck, idolized James so much that he wound up resenting him and ultimately killing him. Director Andrew Dominik told FirstShowing.net that Pitt was the first person he thought of for the role. "Part of the attraction with Jesse James was to cast a movie star and it wouldn't be miscasting, and the celebrity would work for the part rather than against it." (Warner Bros. Pictures) Back to slideshow navigation
  39. Beautiful losers

    Pitt and Jolie arrive at the 64th Annual Golden Globe Awards at the Beverly Hilton on Jan. 15, 2007, in Beverly Hills, Calif. Pitt was nominated for best supporting actor for his role in "Babel," but the award went to Eddie Murphy for "Dreamgirls." (Frazer Harrison / Getty Images) Back to slideshow navigation
  40. Casual stroll

    Jolie holds daughter Zahara, while Pitt props son Maddox up on his shoulders as the family takes a stroll on the seafront promenade in Mumbai, India, on Nov. 12, 2006. Jolie and Pitt were in Mumbai, India's financial hub, to shoot her film "A Mighty Heart," based on the life of the slain Wall Street Journal reporter Daniel Pearl in which Jolie portrays Marianne, Pearl's wife. (AFP - Getty Images) Back to slideshow navigation
  41. Something to 'Babel' about

    Cate Blanchett and Pitt play a couple who run into severe trouble during their vacation in Morocco when Blanchett is accidentally shot. Pitt fights to keep her alive, despite the lack of a hospital or reasonable transportation. Pitt told Interview magazine, "I was just really moved by the last moment, that epiphany of realizing just how close he came to losing everything. It was just that one idea that made me jumpy." (Paramount Vantage) Back to slideshow navigation
  42. World travelers

    Pitt and Jolie ride a motorcycle on a busy street in downtown Ho Chi Minh City, Vietnam, on Nov. 23, 2006. The pair flew to Southeast Asian countries for the filming of "A Mighty Heart" in Mumbai, India. (AFP - Getty Images) Back to slideshow navigation
  43. Chemistry lesson

    Pitt and Jolie created sparks as a bored married couple who discover they are enemy assassins in 2005's "Mr. and Mrs. Smith." Jolie raised eyebrows when she told the New York Times that she'd like to show the movie to her children, because, "Not a lot of people get to see a movie where their parents fell in love." At the time of filming, Pitt was still married to Jennifer Aniston. (20th Century Fox) Back to slideshow navigation
  44. Good deeds

    Pitt visits with children from the Carl Sithole Center orphanage for AIDS-infected and abused children on Nov. 5, 2004, in Johannesburg, South Africa. Pitt traveled to South Africa from Nov. 2 to 9 on a trip organized by DATA, the advocacy group formed by U2 frontman Bono to help fight AIDS, world debt and unfair trade rules. (Getty Images) Back to slideshow navigation
  45. End of an era

    Pitt and Jennifer Aniston attend the 56th Annual Primetime Emmy Awards at the Shrine Auditorium on Sept. 19, 2004, in Los Angeles. The couple divorced in 2005, citing irreconcilable differences. (Carlo Allegri / Getty Images) Back to slideshow navigation
  46. Beefing up

    Pitt played Achilles in 2004's "Troy," an adaptation of Homer's epic about the assault on Troy by the united Greek forces. Pitt told USA Today that he physically prepared for the role for a year and gained about 10 pounds of muscle. "It was grueling," Pitt said. (Warner Bros.) Back to slideshow navigation
  47. Rat Pack redux

    Stephen Soderbergh directed 2001's "Ocean's Eleven," a remake of the 1960 Rat Pack film. The film centered on a gangster named Danny Ocean (George Clooney) who rounds up 10 associates, including Pitt, to simultaneously rob $150 million from three major Las Vegas casinos. At the time of the film's release, Pitt told Film Inside Out, "The great thing about my baggage, as limiting as it may seem, it also sets me up for that kind of surprise and then people go and 'that was great, where did that come from?'" (Warner Bros.) Back to slideshow navigation
  48. Hanging out with 'Friends'

    Pitt guest starred on Aniston's sitcom "Friends" in 2001. In this Thanksgiving episode, Pitt played Will Colbert, a high school friend of Ross' (David Schwimmer) who reveals that he and Ross spread a rumor that Aniston's Rachel was a hermaphrodite and that they were members of the "I Hate Rachel Green Club" in high school. (NBC via Everett Collection) Back to slideshow navigation
  49. D'ya like dags?

    In Guy Ritchie's 2000 film, "Snatch," Pitt played Mickey, an Irish Gypsy boxer who speaks in a barely intelligible Irish accent. Roger Ebert described Pitt's accent by writing, "He sounds like a combination of Adam Sandler and Professor Backwards." (Screen Gems) Back to slideshow navigation
  50. Golden couple

    Pitt and Aniston arrive for the 51st Emmy Awards on Sept. 12, 1999, in Los Angeles. The couple met in 1998 and married in a private ceremony in Malibu on July 29, 2000. (Hector Mata / AFP - Getty Images) Back to slideshow navigation
  51. Ready for a 'Fight'

    Pitt starred as Tyler Durden opposite Edward Norton in 1999's "Fight Club." Norton plays an office drone who is inspired by Durden to start a series of clubs where men can vent their aggressions. Director David Fincher once said, "It's probably a character closer to Brad in real life than most people would be comfortable knowing." (Corbis) Back to slideshow navigation
  52. 'Seven Year' itch

    The 1997 film "Seven Years in Tibet" tells the story of Austian mountaineer Heinrich Harrer (Pitt), who escapes from Austria during World War II in order to climb Mt. Nanga Parabat. He winds up in Lhasa, where he meets the Dalia Lama. The film caused a little bit of controversy when it came out that Harrer had been a member of Hitler's SS elite forces. (TriStar Pictures) Back to slideshow navigation
  53. No surprise

    In 1995, Pitt was chosen by People magazine as the sexiest man alive. He was named sexiest again in 2000. Pitt, pal George Clooney and Richard Gere are the only actors to have received the honor twice. (People) Back to slideshow navigation
  54. 'Monkey' business

    Pitt received an Oscar nomination for his role in 1995's "Twelve Monkeys." Pitt played mental patient Jeffrey Goines, an animal rights activist and anti-consumerist, who plays a crucial role in the life of lead character James Cole (Bruce Willis). (Universal Pictures) Back to slideshow navigation
  55. 'Legend'-ary

    Pitt starred as Tristan Ludlow in 1994's "Legends of the Fall." The film tells the tale of three brothers and their father who live out in the remote wilderness in the 1900s and how their lives are affected by war, love and nature. The film co-starred Anthony Hopkins, Aiden Quinn, Julia Ormond and Henry Thomas. (Corbis) Back to slideshow navigation
  56. Before 'Twilight'

    Pitt starred as vampire Louis de Pointe du Lac in 1994's "Interview With a Vampire," opposite Tom Cruise and a young Kirsten Dunst. In the film, Louis tells how he became a vampire and what the life entailed. (Everett Collection) Back to slideshow navigation
  57. Making the most of a small role

    Pitt dresses down for the "True Romance" premiere in Hollywood, Calif., on Sept. 8, 1993. In the film, penned by Quentin Tarantino, Pitt played the stoner Floyd. His classic moment in the film came when he asked some dangerous gangsters, "You guys want to smoke a bowl?" (Brenda Chase / Getty Images) Back to slideshow navigation
  58. 'Kalifornia' boy

    Pitt played a serial killer in 1993's "Kalifornia," in which he co-starred with Juliette Lewis and David Duchovny. Duchovny plays a journalist who is writing a book about serial killers and happens upon a real one in Pitt. Pitt recently said in Interview magazine of the film, "Apparently the writer hated what I did. It was written more like Martin Sheen in 'Badlands' instead of what I did. I liked it, though." (Everett Collection) Back to slideshow navigation
  59. Ladies' man

    Pitt dated Gwyneth Paltrow from 1995 to 1997. At one point the couple was even engaged to be married. He also dated Juliette Lewis, Robin Givens and actress Jill Schoelen. (Matthew Mendelsohn / Corbis) Back to slideshow navigation
  60. A fish tale

    Robert Redford directed 1992's "A River Runs Through It." Pitt played Paul Maclean, the rebellious son of a Presbyterian minister, who grows up loving to fly fish in rural Montana. Craig Sheffer co-starred as Paul's brother Norm, who is as reserved and practical as his brother is wild. Pitt recently told Rolling Stone that the role was one of his "weakest performances." (Corbis) Back to slideshow navigation
  61. Breakthrough role

    Though it was not his first role by any stretch, 1991's "Thelma & Louise" made audiences sit up and take notice of Pitt. He played J.D., a handsome, young conman who shows Geena Davis' Thelma the pleasures of love making. (Corbis) Back to slideshow navigation
  62. TV star?

    Pitt starred on the short-lived Fox TV series "Glory Days." He played one of four high school buddies who start going in different directions, but who manage to maintain their friendship. The show lasted six episodes. (Everett Collection) Back to slideshow navigation
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