The Legend of Bagger Vance (2000)
Robert Redford directed Damon in this cloyingly cheesy movie. Damon plays a skilled golfer who's traumatised by his experiences in WWI. He gets a chance to turn his life around when mysterious caddy Bagger Vance (Will Smith) arrives and dispenses his uniquely twee wisdom.
Both Damon and Smith feel out of place, and Bagger Vance fails to convince as a sports movie, a romance or a fantasy.
Brainiac Damon? He's on autopilot here.
All the Pretty Horses (2000)
Billy Bob Thornton's adaptation of Cormac McCarthy's novel flopped at the box office, and suffered a critical onslaught, which doesn't seem entirely fair as the film was famously savaged in the edit suite.
As a result, there are inspirational flashes - the impressively mucky cinematography remains undimmed, and Damon gives an appreciably stoic performance - but ultimately it feels incomplete, and moves at a disorientatingly uneven pace.
Brainiac Damon? He lacks the foresight to keep himself out of trouble.
Ocean's Eleven (2001)
Damon's first outing in what would be the first (and least good) of his two big trilogies. Regardless of your thoughts on the next two entries, there's no denying the fact that Eleven is snappy entertainment.
It's almost too slick, but Steven Soderbergh (a frequent Damon collaborator) moves things along with such cool pizzazz that it's impossible not to have a smile on your face throughout.
Brainiac Damon? His pickpocket is the rookie of the team.
Working with Good Will Hunting director Gus Van Sant again, and starring with Ocean's teammate (and childhood friend, of course) Casey Affleck, this existential effort was nowhere near as crowdpleasing as those previous collaborations.
Matt and Casey both play Gerrys, two hikers who get lost in the desert. The film's themes feel like they'd perhaps be better expressed in a novel: on screen the story's simply boring.
Brainiac Damon? Not his most intelligent character.
Spirit: Stallion of the Cimarron (2002)
Matt Damon didn't have the greatest luck when it came to animated movies. After Titan A.E. , he next lent his voice to the four-legged star of this forgettable kids' flick.
The sanctimonious historical context of the story is at odds with the bold, kid-friendly animation, and there's no wit or sparkle to bring any life to the rote, moral-heavy plotting.
Brainiac Damon? As far as horses go...
The Bourne Identity (2002)
The franchise that made Damon a genuine star begins here, in a spy thriller that hits all the right notes, impressing in the action stakes without scrimping on plot or characterisation (the series' tends to cast actors over stars).
At the movie's core is Damon, bringing depth to a potentially blank amnesiac character. Considering the quality of the final outcome, it's hard to believe this went through a troubled production.
Brainiac Damon? He's an action hero whose intelligence thrills as much as his gunplay.
Stuck on You (2003)
A venture into broad comedy wasn't hugely successful for Damon. He makes a decent enough double-act with Greg Kinnear (the pair play conjoined twins), but there's not enough story, or proper laughs, to warrant revisiting this one.
If the supporting cast had have matched up to Damon and Kinnear, maybe this could've gone somewhere. Although, as the Farrelly brothers seem to be playing it safe with their potentially-offensive subject matter, perhaps this was destined to be vanilla.
Brainiac Damon? One of Damon's least intelligent characters (and films).
Although he only appears in a brief cameo, Damon is far and away the highlight in this otherwise forgettable sub- American Pie teen com.
He's almost unrecognisable as the skinhead, punk-band frontman who steals away the lead character's girl (and announces it via the medium of song), spurring the lad on to take a trip to the continent.
Brainiac Damon? Not at all.
The Bourne Supremacy (2004)
Damon was Bourne again (sorry) in this second franchise installment that was every bit as good as the first. Paul Greengrass took the directorial reins, and while his shakey-cam stylings made the action more urgent, there was no intelligence sacrificed.
Supremacy manages to throw in plenty of surprises, and we're forever grateful for finding out that Jason Bourne is capable of defending himself with little more than a rolled-up magazine. It's a credit to the franchise that its popularity snowballed without resorting to lowest-common-denominator tactics.
Brainiac Damon? He's still super-smart, as he gradually delves further into his history.
Ocean's Twelve (2004)
Damon's second Part II of the year wasn't quite so kindly received as Supremacy . While it's simply not as bad as some of the stinking reviews would have you believe, it lacked the straightforward verve of its predecessor.
The infamous Bruce Willis cameo scene is too smug for it's own good, and the final pay-off is immensely underwhelming, but there's still fun to be had here if you fancy giving your brain the night off.
Brainiac Damon? He's still treated like the runt of the litter here.