Matt Damon & Brad Pitt Cameos Turned A 2002 Movie Into An Ocean’s Reunion

Making movies can be hard, unpredictable work, so it makes sense that, prior to beginning principal photography, many directors try to assemble a team of familiar faces and proven talents. John Ford frequently collaborated with producer Merian C. Cooper; screenwriters like Nunnally Johnson, Dudley Nichols, and Frank S. Nugent; and a whole stock company of actors that included Victor McLaglen, Jack Pennick, Harry Carey Jr., and, of course, John Wayne. On a smaller scale, you’ve got Joe Dante, who cast character actor Dick Miller in almost all of his movies, and Ron Howard, who’s been finding small parts for his brother Clint Howard since making his feature directing debut with 1977’s “Grand Theft Auto.”

This cohesion gives film productions a sense of built-in camaraderie and purpose; it also conveys an air of confidence in that everyone working on the movie trusts this group of craftspeople knows how to deliver a high-quality picture.

Obviously, a first-time director generally has to start from scratch in building up these kinds of associations, but if that first-timer happens to be a Hollywood veteran with movie star friends, they can send a clear signal to their cast and crew that this debut movie isn’t the work of a true amateur by casting some pretty big names. And if there isn’t a juicy role for their star buddies, there’s always the opportunity for a cameo. And that’s how Brad Pitt and Matt Damon helped add a touch of sizzle to the first film from one of their showbiz cohorts.

George Clooney’s “Confessions of a Dangerous Mind” was an audacious choice for a directorial debut. The screenplay by Charlie Kaufman is an adaptation of Chuck Barris’ gonzo “unauthorized autobiography” in which the creator of “The Dating Game” and host of “The Gong Show” claimed to have been an undercover assassin for the CIA. Clooney cast Sam Rockwell as Barris and Drew Barrymore as his girlfriend, but found a way to get his “Ocean’s Eleven” co-conspirators involved in big and amusingly minuscule ways.

Pitt and Damon show up ever so briefly as contestants on “The Dating Game.” The boys don’t get any lines; they just sit and listen to their competitor give a ridiculous answer to a ridiculous question from the single woman on the other side of the wall. The joke here is that Clooney got Pitt and Damon to don funky hairpieces and loud ’60s/’70s attire for blink-and-miss-it cameos (which they did as a favor to the director). Unsurprisingly, this moment got a huge laugh when I saw it theatrically. Clooney broadened the “Ocean’s Eleven” reunion by giving Julia Roberts a pivotal role as the untrustworthy CIA operative Patricia Watson. She gets actual lines and much more glamorous attire.

Clooney has subsequently directed eight features and cast Damon as a lead twice (in “The Monuments Men” and “Suburbicon”). As for Roberts and Pitt, he’s continued to work with them as an actor, but has yet to direct them again. It’s probably just a matter of scheduling and not having the right material for them. Or maybe they’re just divas.