Let’s be honest… it’s always a good time to be Brad Pitt. One of the sexiest men alive, rich and powerful, and an extremely underrated actor, he’s considered a shoe-in for a Best Actor nomination for Money Ball, out on DVD and Blu-Ray this week. He’s excellent in the film, which reminded us that beyond his good looks he’s appeared in a number of modern classics worthy of mention in our ongoing series Five Great Movies.

William Bradley “Brad” Pitt first appeared uncredited in non-speaking parts in the likes of Hunk and No Way Out before moving to roles in the daytime soap opera Another World and the nighttime soap opera Dallas in 1987. From there he shuffled between minor film and television gigs until his breakout supporting turn as a seductive hitchhiker in Ridley Scott’s Thelma and Louise, from which he steadily increased his star power. Nowadays he headlines major summer blockbusters and art house hits alike, when he’s not living your personal dream in a big fancy house with Angelina Jolie.

So here are five particularly great films from his body of work. Not necessarily the best, mind you, just five great ones. Not your favorites? Tell us your picks in the comments below.


SE7EN (dir. David Fincher, 1995)

Brad Pitt was already a bona fide star by 1995, having appeared in such high profile films as A River Runs Through It and Interview with a Vampire. (We’ll give him a pass on Cool World.) But 1995 was the year that really made him as an actor, starting with the cloyingly spelled Se7en, which was also the film that made David Fincher the household name he is today.

The incredibly dark serial killer drama starred Morgan Freeman and Brad Pitt as homicide detectives – Freeman as an exhausted veteran on the edge of retirement, Pitt his hotheaded young replacement – on the trail of an unusually creative murderer who selects his victims, and their punishments, based on the Seven Deadly Sins. A gluttonous man is forced to eat until his stomach bursts, a greedy man forced to slice off a pound of his own flesh (a scholarly reference to Shakespeare’s The Merchant of Venice). Andrew Kevin Walker’s screenplay eschewed gunfights and car chases in favor of moody character work and genuinely unexpected twists, and Fincher shot the film in a gorgeously atmospheric but surprisingly subdued editing style, particularly for an “MTV” director. Freeman technically drives the movie, but Pitt broke out in his role as a cop who’s passionate to a severe fault. The film’s now-iconic ending would have buckled under the weight of a less talented actor. Although Se7en led to a string of inferior copycat movies like Taking Lives and Suspect Zero, it remains a superior dramatic thriller thanks to the filmmakers’ balance of style and restraint, and the excellent performances from its cast.


TWELVE MONKEYS (dir. Terry Gilliam, 1995)

Twelve Monkeys is one of the most successful films in former Monty Python member Terry Gilliam’s career. Ironically, it’s not his best remembered. Kookier flicks like Time Bandits and Brazil get all the attention. But this eerie and unsettling time travel thriller, based on Chris Marker’s also-excellent short film La Jetée, was the second half of the one-two punch that caused Brad Pitt to break out as a serious actor in 1995. He was rewarded with a Golden Globe and an Oscar nomination for Best Supporting Actor. He won the Globe, but lost the Academy Award to Kevin Spacey’s exceptional turn in The Usual Suspects.

Bruce Willis stars as James Cole, a convict in a virus-torn future who’s sent back in time to research the start of the plague, and hopefully bring back a sample of the original strain in order to save what’s left of humanity. His initial trip sends him back six years early, where he’s institutionalized for obvious reasons. There he meets Jeffrey Goines, played with manic glee by Pitt. Goines is a radical animal rights activist who listens a little too closely to Cole’s descriptions of the future. When Cole finally ends up where/when he’s supposed to be, he realizes that he might have inadvertently kick-started the plague by inspiring Goines’ eco-terrorism, and has to do whatever he can to stop the chain of events he thinks he caused. Or is he overthinking it? Can the future be changed at all? For a generally fantastical director, Gilliam does a great job with this sci-fi thriller. The future is unusually designed, but he mostly lets the speak for itself with its crackerjack screenplay, punctuated by Pitt’s scene-stealing performance.


FIGHT CLUB (dir. David Fincher, 1999)

1999 is destined to go down as one of the best years in film history, thanks to a seemingly non-stop parade of instant classics like American Beauty, Three Kings, Being John Malkovich, The Matrix, The Sixth Sense and, perhaps at the top of the list, David Fincher’s Fight Club. Fincher reteamed with Brad Pitt for the adaptation of Chuck Palahniuk’s dangerous novel about repressed male urges in an oppressively politically correct and consumer-driven modern landscape, which only thinly hides a dark underbelly of corruption, violence and terror. It’s also funny as hell, thanks to Pitt’s exceptional performance as Tyler Durden, quite literally the id personified.

Describing the plot of Fight Club is perhaps too complex to get into here. Saying it’s the tale of a repressed insomniac played by Ed Norton who teams up with a mysterious ideologue, played by Pitt, to form an underground bare knuckle-fighting league which spirals dangerously out of control only touches the surface. The film was a box office bomb upon its release, but quickly found a home amongst disenfranchised youths who responded to the characters’ frustrations with a “polite” society with no outlet for masculine, even violent frustration. But times have changed, the wars Tyler Durden complained were absent from the social landscape have once again reared their ugly heads, and the film, although as brilliant as ever, may no longer be as pertinent as it was upon its initial release. That said, it’s still the dark, funny, scary and f**ked up testament to Fincher’s and Palahniuk’s anarchic predilections, and to Pitt in particular, who in Tyler Durden crafted a rebel icon worthy of comparison to Marlon Brando in The Wild Ones.


THE TREE OF LIFE (dir. Terrence Malick, 2011)

It feels like cheating, but screw it, let’s fast forward to this very year with The Tree of Life, a film by the legendary filmmaker Terrence Malick. He’s only directed a handful of movies, but they are, in their elegiac way, all classics. The Tree of Life is no exception. Pitt produced the movie, and after the tragic loss of Heath Ledger took over in one of the lead roles as an angry father fighting for the philosophical upbringing of his young sons with their mother, played by Jessica Chastain in her breakout performance.

Terrence Malick’s most recent films in particular seem to include their plots as an afterthought. He’s after something far more cosmic than that. In The Tree of Life he uses the simple story of a family in Texas as a focal point for deeper reflections on the nature of life as a whole, connecting the story of Pitt’s family to such grand events as the very formation of the universe and the end of life itself. These concepts are explored, but perhaps difficult to latch on to. If these ruminations seem pretentious to you, focus instead on the way in which Malick tells his main story, as recalled by one of Pitt’s sons, played by Sean Penn as a middle-aged man. The Tree of Life unfolds not as a proper narrative, but as if sifting through an individual’s memories. The earlier the events in the film, the more enigmatic and visceral they appear, free of more than a snippet of dialogue or an overarching plotline. As the protagonist ages, the film lingers longer on key incidents, perhaps not outwardly important ones, that influenced who he became as an adult. Chastain’s getting most of the accolades, but Pitt carries the brunt of the film’s conflict as a frustrated man who perhaps subconsciously infuses his sons with an inner conflict equal to his own. It may not sound like a “fun” film, but The Tree of Life is after something more consequential than that, and succeeds on a level with few peers.


MONEYBALL (dir. Bennett Miller, 2011)

Pitt’s most recent film, Moneyball, is yet another of his best films. This time Pitt gets a proper starring role as a Billy Beane, the general manager of the Oakland A’s who, in a fit of frustration, bucks all notions of athletic romanticism in favor of an untested managerial style based purely on statistics. Director Bennett Miller’s film never forgets to be rousing – it’s still the tale of an underdog baseball team beating the odds – but it’s also a smart, character-driven drama that personifies the individualistic ideals of Ayn Rand better than the film version of Atlas Shrugged ever does. Whether or not you agree with her philosophies, it’s fair to say that this is the best cinematic example yet of how to portray them.

As Beane, Pitt has a difficult job, both as an actor and a character. Beane is tasked with forming a winning baseball team without the financial resources available to his competitors. Teaming up with the clever but inexperienced statistics nerd Peter Brand, played by Jonah Hill, he forms a baseball team which, on the surface, appears to be a lackluster group. But they want to depend on easily traded superstars, they want players who can get on the base regardless of any perceived deficiences. This places Beane and Brand at odds with the baseball world at large, including their own coach, played with believable weariness by Philip Seymour Hoffman, who refuses to play the game their way for fear of losing his credibility. Their struggles to change the way the sport is played makes them bigger underdogs than even the Oakland A’s, making their eventual, mostly victory extremely satisfying. Pitt’s character is a complex one, however, applying an objective look at his job that he can’t quite fit into his family life. It’s that second part which ironically tears him down, sidelining the rest of his career, and confirming the film’s individualist ideals better than mere success ever could. It’s a smart, powerful sports movie that has more on its mind than you’d ever expect.


Come back next week for more Five Great Movies!