Saving Private Ryan” (1998)
In the summer of 1998, just a few short months after winning the Oscar for Best Original Screenplay for “Good Will Hunting,” Matt Damon and Ben Affleck’s next films would show just how divergent their career paths would become. Damon’s next project was a supporting part in Steven Spielberg’s WWII epic, while Affleck’s was a starring role in Michael Bay’s giant asteroid film “Armageddon.” Though his character’s name is in the title, Damon’s role, though integral, was truly a supporting one, not appearing in the film until an hour and 46 minutes in. Despite his lack of screen time, Damon leaves a strong impression in the film thanks to a monologue about his brothers that was apparently improvised by Damon. The rest of the ensemble, headed up by Tom Hanks, was filled out with a mix of character actors and up-and-comers like Edward Burns, Tom Sizemore, Barry Pepper, Adam Goldberg, Vin Diesel, Giovanni Ribisi, Jeremy Davies and Paul Giamatti, among others. Spielberg’s film, for which he won his 2nd Best Director statuette, has not aged entirely gracefully. The present day bookends are the director at his most cloyingly sentimental, but the D-Day landing at Normandy still ranks as one of the most chaotic, visceral depictions of war ever put on film. [B+]

Rounders” (1998)
Matt Damon's first lead following the success of "Good Will Hunting," "Rounders" was mostly ignored on its debut, but has evolved into something of a cult hit over the years. The actor plays Mike, a poker whiz who's promised his girlfriend (Gretchen Mol) that he'll give the game up and focus on his law school studies. But when his no-good best pal Worm (Edward Norton) is released from prison, he's dragged back into gambling to save his pal from the sinister Russian mobster Teddy KGB (a ludicrously enjoyably over-the-top John Malkovich), the same man who ended Mike's career years earlier. While it's beloved most by poker fans (it's probably the best depiction of the game to date), the film in general is firmly entertaining -- director John Dahl gives a terrific noirish tinge to the film, the script is zingy, and most of the performances -- Norton and John Turturro in particular -- are excellent. If the film has a flaw, it's actually Damon; like many of his earlier films, he's engaging, but a little bland. Still, we'd certainly be keen to see the long-promised sequel, if it ever materialized. [B]

The Talented Mr. Ripley” (1999)
It would have been just too easy for Matt Damon to trade in on his matinee idol good looks and collect paychecks for action movies and rom-coms. Instead, he pushes himself to physically disappear into his psychologically complex roles, using physical characteristics -- a paunch, a crew cut or a pair of horn-rimmed glasses -- as his entry into such enigmatic characters. His glasses are the totem of Tom the imposter in “The Talented Mr. Ripley,” the transformative role as the insidious grifter that announced Damon as a serious thesp, no vain pretty boy. Your average actor wouldn’t necessarily choose to take on the role of the homicidal sociopath in a gay panic, but Damon’s not your average actor. He’s made a practice of playing characters in identity crisis (“Good Will Hunting,” ‘Bourne,’ “The Informant!”) and ‘Ripley,’ was one of the first times he displayed his true virtuosity in embodying this conundrum. Damon’s most indelible characters are always striving to achieve some station in life that is almost impossible for them to gain, and Tom Ripley is the ultimate showcase for his ability to display the many emotional states of such nuanced, complicated people. He is simultaneously dorky, naive, seductive, hopeless, creepy and terrifying in Anthony Minghella’s adaptation of the Patricia Highsmith novel; the different emotions effortlessly cascading across his face. Damon is the type of post-modern actor that turns up his snub nose at the idea of a star persona and lets the characters completely take over, and ‘Ripley’ was his definitive announcement that he was here to ACT, not be a movie star. [A]