Welcome to 5 Favorites. Each week, I will put together a list of my 5 favorites (films, performances, whatever strikes my fancy) along with commentary on a given topic each week, usually in relation to a specific film releasing that week.

Who would have thought that the kid who starred in Good Will Hunting would turn into one of our finest actors. A lot of people, actually. Both he and Affleck showed a lot of promise with that film, especially the screenplay. However, Damon was front-and-center on the big screen and ably carried the effort on his shoulders. Affleck had a minor role that gave us little indication of his potential. Damon has a new film coming out this weekend where he stars as a Midwestern farmer who travels to Europe in order to prove his daughter’s (Abigail Breslin) innocence. The film is directed by Best Picture-winning filmmaker Tom McCarthy (Spotlight) and has already earned strong reviews out of its Cannes Film Festival debut. This week, I’m going to look Matt Damon’s 30-year career and select five of his best movies.

The Talented Mr. Ripley (1999)

Although Damon had developed something of an everyman persona for himself through his early screen roles, he took a decidedly twisted turn with his appearance in Anthony Minghella’s adaptation of a Patricia Highsmight novel. In the film, Damon plays a grifter who is asked to convince a wealthy father’s wayward son (Jude Law) to come home. During his paid-for trip to Italy he has an affair with Cate Blanchett and becomes friends with Law and his girlfriend Gwyneth Paltrow. Also involved is Philip Seymour Hoffman as Law’s friend.

In this tangled web of murder and intrigue, Damon remains an enigmatic figure, charming enough to convince others of his innocence while cunning enough to escape culpability in the deaths of Hoffman and Law. Even as his house of cards comes crashing down, Damon manages to outwit and outthink everyone around him, making for a rare situation where the film’s villain is victorious rather than being brought down for his crimes. Damon is fantastic in the film as is the rest of the cast. Minghella was one of our finest directors at the time and this film helped secure his place in cinema history. It also displayed Damon’s inestimable talents.

The Bourne Identity (2002)

With the huge successes of Good Will Hunting, Saving Private Ryan, and Ocean’s Eleven under his belt, Damon was perceived as an immense talent with a dutiful following that combined to make him the perfect actor to embody the spy Jason Bourne in the big screen adaptation of Robert Ludlum’s The Bourne Identity. In the hands of director Doug Liman and screenwriters Tony Gilroy and William Blake Herron, Bourne builds on Damon’s natural charm to create a modern, gritty spy thriller with a character that’s as vicious and calculating as James Bond is suave and debonair.

At the film’s open, Bourne is adrift with gunshot wounds and a complete lack of memory about what led him to this precarious position. The film follows Bourne as he tries to reassemble his identity. The international intrigue and conspiracies that have led him to this juncture prove overwhelming, but his skill as a trained operative keep him on the track of whatever duplicitous events are transpiring. The Bourne Identity stands well, alongside the Bond filmsb as an exemplary piece of genre filmmaking. Afterwards, you won’t be able to imagine anyone else in the role, even the man who ultimately replaced him (briefly) several years later, Jeremy Renner.

The Brothers Grimm (2005)

Twisting the concepts behind the works of the Brothers Grimm, acclaimed director Terry Gilliam helps weave a fascinating story that feature the brothers (Damon & Heath Ledger) as famed monster hunters who are actually conmen fleecing unsuspecting villages with fake monsters and victories. When their elaborate ruse is threatened by the constabulary, the pair are forced to help solve the mysterious disappearances of several young girls in a small town.

Gilliam was directing from a script by Ehren Kruger and the film co-starred Peter Stormare, Lena Headey, Jonathan Pryce, and Monica Bellucci. Gilliam’s trademark whimsy comes through quite well in a strange concoction of fairy tale and horror. It’s a funny film that features a strong cast, including Damon, with a beautiful production and costume design. While the film wasn’t as popular as it should have been, it’s an enjoyable romp that should appeal more to fans of Gilliam than to the fans of any specific actor in the picture.

The Martian (2015)

The recent career of director Ridley Scott has been a mixed bag of mediocre films supported by wonderful adventures like this one. The Martian is based on a novel by Andy Weir and revolves around an astronaut abandoned on Mars who must use his knowledge and wits to survive until a rescue can be mounted. Back on Earth, the incident has gained a lot of attention, especially when it’s decided that it would be too costly to rescue one man stuck millions of miles away. That doesn’t sit well with Damon’s crew who embark on a return journey to collect their missing comrade.

Scott emerged from the late 70s and early 80s as one of the preeminent science fiction filmmakers with the twin successes of Alien and Blade Runner bolstering his career ahead of his 1991 Oscar-nominated feature Thelma & Louise, which together made him one of the most important filmmakers of his generation. Although his subsequent career has been a rocky hodge podge, The Martian was a return to form for the director, turning out his best film since Thelma & Louise over 20 years earlier. Damon employs his estimable charm to carry a film that has the occasional diversion to other events in other locales, but we’re always glad to be back with him when we return.

Downsizing (2017)

Perhaps one of the more unusual films Damon has ever appeared in, Downsizing was Alexander Payne and Jim Taylor’s fascinating sci-fi drama about human beings in financial distress who agree to be shrunk down and sequestered in a massive compound of tiny houses and even tinier citizens. It’s all done in the guise of helping reduce human civilization’s carbon footprint and to aid in decreasing the effects of climate change. Damon and Kristen Wiig play a financially strapped couple who decide to undergo the procedure. At the last minute, Wiig bails leaving Damon alone in a miniaturized community in New Mexico.

The film progresses through his struggles with self-identity and loneliness only to discover a large number of individuals with whom he shares his ideals and passions, ultimately embarking on a journey of growth. Damon is a charismatic lead once again, but the bizarre situations in which he finds himself are what make the film most intriguing. Toss in terrific performances from the likes of Wiig, Christoph Waltz, Hong Chau, and Jason Sudeikis as well as a hilarious cameo appearance by Neil Patrick Harris and Laura Dern and you have a well acted, engaging picture. It’s a funny film with an important message, but for a lot of people, it might feel a bit preachy. Regardless, Damon’s strength as an actor helps carry the film above its narrative quirks and keeps the film feeling grounded even when it is at its most outlandish.