From our first awareness of him as a celebrity, Matt Damon seemed designed to annoy us. He appeared as if out of nowhere at the end of 1997, starring in “The Rainmaker” and then starring and co-writing “Good Will Hunting” with Ben Affleck. The press ate them up with a spoon: they were young, conventionally attractive (if somewhat fratty), and had addressed their borderline failures as actors by writing a film vehicle to star in — one which went on to earn nine Oscar nominations and two awards, including the prize for best screenplay for BFF Affleck and Damon to share. So completely had they started to believe their own hype as America’s Boy Sweethearts — and so game were they to feed it — that their dates for the 1998 Oscars were their moms. All together now: awwwwwww!
The backlash started shortly thereafter. They made some flops, they dated some fellow celebrities, and when they were paired up again on screen, no one cared. When the millennium arrived, they each regrouped and took stock. Ben Affleck did everything the same: more bad Michael Bay movies, more bad Kevin Smith movies, more boring action movies, and more celebrity girlfriends. (Hey, did you know he dated Jennifer Lopez for a while? He did! You’d think the media would have picked up on that.) But what of Matt Damon? Has his most recent work onscreen won us over again?
Tara Ariano
There’s no “again,” as far as I’m concerned. “Good Will Hunting” didn’t work on me; I thought it was self-indulgent and — to paraphrase comedian Paul F. Tompkins — expressly designed to get Damon lots of...well, this being a family Web site, I can’t use the word Tompkins did, but “feminine attention” would be a decent euphemism. And it’s hard to watch the movie and deny that that’s the case: Will Hunting is super-smart, but troubled! He’s charming, but emotionally unavailable! He’ll love you up right, take you out for a fun afternoon at the dog track, and then stub out his cigarette on your heart! But maybe all he needs is the love of the right woman! It’s a screen archetype we’ve totally never seen before!
Sarah Bunting
I’ve always liked Matt Damon; I enjoyed “Good Will Hunting,” although I felt it could have used 100 percent less Robin Williams, and in spite of that rack of tombstones Damon’s trying to pass off as “teeth,” I think he’s kind of cute, too. (What can I say, I like ’em a little fratty.)
I especially liked Damon’s willingness to take risky parts — such as his all-but-forgotten role as anti-Semite ringleader Charlie Dillon in “School Ties,” which he managed to lend nuance in spite of clunky dialogue and the scenery-chew-a-thon going on all around him. He's also willing to make fun of himself, the way he did in “Chasing Amy” and “Confessions of a Dangerous Mind.” I even liked “Rounders,” at least when Gretchen Mol wasn’t on screen. Damon just seems likable — the kind of guy you’d enjoy hanging out with.
Tara
But Sarah, the flops! Each floppier than the last: “Titan A.E.,” “The Legend of Bagger Vance,” “All the Pretty Horses.” All pure, unadulterated, Grade A Tara repellent.
Dude. Wait. Which side am I arguing?
Sarah
If it’s the side where “All the Pretty Horses” should be taken behind the barn and shot, girl, move over.
Actually, I think you’re arguing the side that states Damon’s career has improved after a rocky and uncompelling start. I’m more inclined to say that, while I like some Damon movies, he’s still really inconsistent; for every project he does that’s good, there’s another one that’s weak.
Of course, compared to Affleck, he’s on a serious roll, but 1) who isn’t, compared to Affleck, and 2) when you look at his IMDb entry, he looks very ambitious, but without regard to quality. Damon’s career plan apparently goes something like “work with prestigious and/or ‘It’ directors; don’t bother to vet the script or my co-stars first.” Sometimes the strategy succeeds; Steven Soderbergh’s “Ocean’s Eleven” is awesome and I can’t wait for the sequel.
Often, though, the strategy backfires, and the bombiest bombs on Damon’s resumé come from the most respected directors. The boring and misconceived “All The Pretty Horses,” which also featured the boring and misconceived Penélope Cruz? Directed by then-hot director (and current antique-ophobe) Billy Bob Thornton. The criminally tedious “Legend of Bagger Vance”? Directed by Robert Redford. “The Talented Mr. Ripley” — which, um, isn’t — directed by Anthony Minghella.
It’s a smart tactic, working with the big shots in the industry, but not if the scripts stink, and not if Damon’s miscast.
Tara
Yeah, the idea that Damon’s Tom Ripley could fool anyone into thinking he was Dickie Greenleaf — played by Jude Law as a golden Adonis — is kind of preposterous. Damon’s cute, but Law is kind of otherworldly.
Anyway, Damon’s career did a 180 after “Horses” that seemed specifically tailored to me. Maybe he got me in the sights of a spy satellite, noticed I was avoiding everything he did, and decided his new career strategy was only to make movies (and TV guest appearances) I would enjoy. The “Ocean’s Eleven” remake is one of the all-time best heist comedies ever. “The Bourne Identity” is a fine, unpredictable spy caper that doesn’t take itself too seriously, and is filled out with great supporting actors. His guest spot on “Will & Grace” — as a straight man passing in the Gay Men’s Chorus in order to join its European tour — was effectively subtle (a rarity on that show) and had a nice throwaway joke about the rumors that he and Affleck are more than good friends.
But really, the proof that Damon is making movies for me alone is the silly but endearing conjoined-twins comedy “Stuck On You.” And I know it was made for me alone because I am the only person on the continent who saw it.
Sarah
True. Lord knows I didn’t see it — but that movie is exactly what I mean. Was it a bad idea for Damon to do a Farrelly Brothers movie? Not at all; they’re bankable comedy producers. Should he have realized that Greg Kinnear’s hideous fright wig would keep audiences away in terrified droves? Yes. Yes, he should have. Because ew.
But the problem I see is that he’s playing it safe, trying to “Ishtar”-proof himself by working with “prestige” people – and it’s not really helping him.
The “Bourne” franchise is a perfect example. I wouldn’t have called him for an action hero, but it worked in “The Bourne Identity,” which I enjoyed. But that seems safe and predictable, too — he’s positioning himself as the heir to Harrison Ford, and it’s not that Ford doesn’t need an heir (not to mention some dating advice), but haven’t we seen someone attempt this maneuver before? Someone who starred in “The Sum Of All Fears,” and whose name rhymes with “Men Chaffleck”?
Tara
I never thought the day would come that I’d feel Matt Damon had earned the right for me to stop calling him “Pigboy.” But he has.
Sarah
Damon doesn’t have to win me over; I liked him to start out with. But he needs to start reading the scripts before he agrees to do the movies. Yeah, next year’s “The Brothers Grimm” sounds good on paper — it’s directed by Terry Gilliam. But Gilliam’s last project got canned mid-production, and Heath “That’s ‘Mr. Wooden’ To You” Ledger is co-starring, and it sounds to me like Damon is going to have to wear period clothing, which…no. He’s running out of room to make mistakes.
Tara Ariano and Sarah D. Bunting are co-creators and co-editors of