Look up the definition of “cool actors" and you'll see pictures of George Clooney and Brad Pitt. The Oscar winners are the complete package: talented, handsome and charming. So when actors like Pitt and Clooney combine forces to collaborate on a film, it becomes a noteworthy pop culture moment.
The latest Clooney and Pitt collaboration will be in “Wolfs,” Jon Watt’s Apple TV Plus action-comedy where the two stars play fixers who reluctantly work together on a job. In honor of “Wolfs,” which drops Sept. 27, we ranked Clooney and Pitt’s best collaborations.
5. ‘Confessions of a Dangerous Mind’
“Confessions of a Dangerous Mind” isn’t a true collaboration between Clooney and Pitt, with the latter only making a cameo as a bachelor on a dating game. Therefore, it comes in at No. 5 because of technicality, even though it’s better than some of the movies where they both have more significant roles.
That being said, “Confessions of a Dangerous Mind” is an important film in Clooney’s career since it's his directorial debut. The story revolves around Chuck Barris (Sam Rockwell), the creator of “The Dating Game” and host of “The Gong Show.” Barris lived a double life as a CIA assassin, or at least that’s what he claims. Don’t worry about the validity of Barris’ account. Enjoy the stylish direction from Clooney and spot-on performance from Rockwell in one of his career-defining roles.
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4. ‘Ocean’s Twelve’
You got to hand it to Soderbergh. He always takes risks and never rests on his laurels. Instead of doing a paint-by-numbers sequel to “Ocean’s Eleven,” Soderbergh plays the long con and adds in more twists, with mixed results. Terry Benedict (Andy Garcia) wants his money back, so he kidnaps Danny (Clooney), Rusty, (Pitt), Linus (Damon) and others and demands to be repaid. Without enough money, Terry gives Danny and his crew two weeks to come up with the cash. If Danny and his crew steal a valuable egg before another thief (Vincent Cassel), they will win the money to pay back Benedict.
One of the most controversial plot points involves Tess Ocean (Roberts) pretending to be Julia Roberts in a scene with Bruce Willis. Again, the meta storyline will not be for everyone. Still, “Ocean’s Twelve” is Clooney, Pitt, and Damon having the time of their lives playing characters they know inside and out. That’s fine with us.
3. ‘Ocean’s Thirteen’
In “Ocean’s Thirteen,” the gang gets back together, and this time, it’s extra-personal. Danny’s friend, Reuben Tishkoff (Elliot Gould), partners with casino tycoon Willy Bank (Al Pacino) to build another hotel/casino in Las Vegas. Bank eventually swindles Reuben into signing over ownership to cut him out of any financial benefits. Devastated and embarrassed, Rebeun suffers a heart attack.
When Danny tries to make things right, Bank refuses and continues on with his plan to open the hotel. Bad move because Danny gathers his crew to ruin and bankrupt Bank’s hotel. “Ocean’s Thirteen” returns to the “Ocean’s Eleven” playbook, and lets the audience have fun with these characters for one last time. It’s the cherry on top for a terrific trilogy.
2. ‘Burn After Reading’
The Coen brothers are on the shortlist of directors who have mastered black comedy. The duo’s cynicism is one of their best assets. They never shy away from death and always have a knack for spotlighting lovably dumb characters in intricate stories. In layman’s terms, “Burn After Reading” features a bunch of idiots in an unexpectedly dark movie.
A disgruntled CIA analyst, Osborne Cox (John Malkovich), abruptly quits his position and plans to write a memoir about his time in the organization. His writings accidentally get into the hands of two brainless gym employees, Linda Litzke (Frances McDormand) and Chad Feldheimer (Pitt), who plan to sell them for money. The wild card in the scenario is Harry Pfarrer (Clooney), a U.S. Marshal who becomes intertwined with both parties. Clooney and Pitt are fearless in this movie, as they try to out-idiot one another in this amusing crime comedy.
1. ‘Ocean’s Eleven’
“Ocean’s Eleven” in three phrases: five stars, perfect movie, no notes. Steven Soderbergh crafted the coolest heist movie with “Ocean’s Eleven,” a remake of the Rat Pack movie from 1960. After a four-year stint in prison, Danny Ocean (Clooney) recruits his friend Rusty Ryan (Pitt) to pull off the ultimate heist: rob three Las Vegas casinos for $150 million. This robbery is personal for Danny because the casino’s owner, Terry Benedict (Andy Garcia), is dating his ex-wife, Tess Ocean (Roberts).
Like many heist movies, Danny and Rusty need a crew, so they assemble a group of eclectic characters to execute their mission, including Linus Caldwell (Damon). With slick direction from Soderbergh and vibrant charisma from the leads, “Ocean’s Eleven” is as fun of a time as you’ll ever have to watch a movie.
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