For over two decades, Oscar nominee Matt Damon has been one of the most reliable leading men in Hollywood. While with “Good Will Hunting” (1997), Damon and his childhood friend Ben Affleck became celebrities by writing their own ticket to fame and riches, the pair had been acting for years before that film became an art-house success, including starring in “School Ties” (1992) together. But it was to share the interesting tale of a hidden math genius (Damon) by returning to their native Boston that put them on the map, earning them an Oscar for Best Original Screenplay and giving Damon his first nomination for Best Actor.

THE TALENTED MR. RIPLEY

In “The Talented Mr Ripley,” Damon uses his everyman charisma to chilling effect, making our skin crawl like an average nobody who lies, cheats and murders his way into being someone. Adapted from Patricia Highsmith’s classic novel by Anthony Minghella, it sees lonely grifter Tom Ripley (Damon) finagling his way into the inner circle of wealthy playboy Dickie Greenleaf (Jude Law), who, with his sister, Marge (Gwyneth Paltrow), lives in Italy. Yet he takes desperate measures to cling on as Ripley’s current social status threatens to collapse. Despite winning an offer for the Golden Globe, Damon was snubbed for Best Actor at the Oscars, which is totally criminal.

GOODWILL HUNTING

By penning this heart-tugging inspiring romance for his friend Ben Affleck, Damon hit the Oscar jackpot. “Great Will Hunting,” directed by Gus Van Sant, focuses on a South Boston janitor (Damon) working at MIT who is actually a math genius. It’s up to a university counsellor (Robin Williams, recipient of Best Supporting Actor) to expose the deep scars of Will’s history so that he can have a happier life. There’s a wealth of fantastic supporting characters here, including Will’s partner Minnie Driver and Affleck as his best friend. Damon also received his first Best Actor nomination for his tender, complex performance, in addition to his screenwriting triumph.

THE MARTIAN

Although others would lift their eyebrows at its description as a musical or sitcom (which the Golden Globes had no issue with), the high entertainment appeal of the sci-fi adventure of Ridley Scott is not disputed. Damon stars as Mark Watney, an astronaut who, after his team thinks he is dead, becomes trapped on Mars. Instead of giving up, he depends on his imagination to stay alive long enough for NASA to send a rescue mission (including growing potatoes in its own waste). With their Best Comedy / Musical Actor award, Globe voters awarded Damon’s relentlessly charming performance, while he was nominated as Best Actor by the Academy.

True Grit

The first collaboration of Damon with Joel and Ethan Coen can feature the funniest performance of the actor to date. Damon plays LaBoeuf (La-Beef), a dimwitted Texas Ranger charged with hunting down a murderer named Tom Chaney in the remake of the 1969 revenge western. In the way, in order to achieve peace, LaBoeuf aligns with one-eyed drunken sniper Rooster Cogburn (Jeff Bridges) and young Mattie Ross (Hailee Steinfeld). The film needs to be called The Odd Throuple!

Ocean’s Eleven

The Sin City heist film Ocean’s Eleven by Steven Soderbergh was never supposed to become a franchise trilogy, but just an entertaining remake of the 1960 Rat Pack film. And you wonder why the first is outstripping the other two! In the movie, Damon plays Linus Caldwell, a young thief who is continually ribbed by his upperclassmen, Danny (George Clooney) and Rusty (Brad Pitt), and needled. Yet in the end, it’s the cunning of Linus that proves crucial to the success of a $150 million triple casino heist in Las Vegas. Hey, Linus is not, after all, a wet towel!

FORD V FERRARI

The high-octane racing drama of James Mangold can allegedly be about the efforts of the Ford Motor Corporation to create a car to race in the 1966 Le Mans tournament, but it is actually about the friendship between the two men charged with producing it. There’s Carroll Shelby (Damon), a former driver hired to design the car by Ford. And there’s Ken Miles (Christian Bale), drafted by the British hotshot to force it. They come up with a vehicle by trial and error to contend with Italian auto maestro Enzo Ferrari in the famed 24 Hour Racing Championship, forming a relationship along the way. For its video editing and sound editing, the film received four Oscar nominations, including Best Picture.

SAVING PRIVATE RYAN

Damon is the driving force behind the WWII epic of Steven Spielberg, playing the titular Private Ryan who needs saving, while his screen time is minimal. Since his three brothers were killed in action, Tom Hanks shines as the platoon leader sent behind enemy lines to rescue the lost paratrooper. Damon arrives late in the film and, with a deeply moving monologue about growing up with his late siblings, makes the most of his role. And with his gritty, handheld realism, particularly in the opening sequence, Spielberg, who won his second Oscar as Best Director for the film, stuns us with a 40-minute reconstruction of the Normandy Landings.