The seventy-four-year-old veteran actor, director, and producer Michael Douglas just got his star on the Hollywood Walk of Fame! For the prestigious event, he was accompanied by his wife, Catherine Zeta-Jones, and his hundred and one-year-old father, the legendary Spartacus himself, Kirk Douglas.

Michael’s career has spanned over five decades, and he’s won many awards including an Academy Award for his portrayal of the infamous corporate raider Gordon Gecko in Oliver Stone’s Wall Street. He also won an Oscar as a producer for the 1975 groundbreaking sleeper One Flew Over the Cuckoo’s Nest.

In honor of his achievements, we thought we’d take a look at some of Michael’s best, most iconic, quirky, classic roles as well as his under-appreciated ones.

Wonder Boys

Michael Douglas is utterly pathetic and absolutely endearing as professor Grady Tripp in Curtis Hanson’s stoner literary classic Wonder Boys. Michael plays the hapless, intoxicated professor given to Grand Mal seizures to hilarious, as well as dreamy, effect. Taking his suicidal, old movie-obsessed student (Toby McGuire) under his wing, Grady proceeds to shoot the Chancellor’s dog, aid in the theft of Marilyn Monroe’s shawl, and lose his 2,000 page novel in the course of a weekend.  

Robert Downey Jr. is just wicked as Grady’s impulsive editor, Terry Crabtree. Katie Holmes gives another solid indie performance as Tripp’s captivating student, Hannah Green. And Frances McDormand is perfectly fit for the role of Grady’s mistress, Professor Gaskell, Dean of the Academy. It’s all a lovely comedy of errors with Douglas carrying the whole sad, impossible sack on his capable shoulders.

The Game

In the 1997 mystery thriller The Game, we have Michael playing yet again the ultimate silver spoon-fed–even though he eats a cheeseburger and a cupcake on his birthday–American businessman, and doing it to perfection! Douglas’ Nicholas Van Orton has had to take the reigns of the family estate after his father, a corporate Barron himself, commits suicide. Nicholas is plagued by his flaky younger brother, Conrad, played by a mercurial Sean Penn and the one that got away, his ex wife, Elizabeth. Van Orton agrees to participate in a curious game, and his life quickly spirals out of control. Nicholas’ journey is indeed circuitous and strange, but it’s the verisimilitude, the bewilderment, and the ominous resonance that Douglas displays–as a man who’s had it all and lost it all–that is absolutely on point.

Falling Down

In Falling Down, Michael Douglas took a real risk and played defiantly–and indeed violently–against character, portraying the mad-as-hell and not-going-to-take-it-anymore D-Fens. Michael eschews the perfectly-coiffed hair and the silky smooth delivery and replaces his affluent demeanor and ubiquitous nature with a rigid 1950’s-era brush cut, a briefcase that seems like an anchor for his very soul, a crisp nerd pen packet, and a boulder on his shoulder that could crush a Trans Am.

Although there are a number of stellar supporting performances here, it’s really all about D-Fens and his screed on modern society. Go to any random Falling Down clip on YouTube, and you’ll see that this film strikes a real cord for those who feel misunderstood, demeaned, disgusted, and for those who are just plain in a savage mood.

The Streets of San Francisco

Michael proved to be a natural right from the start with his portrayal of the green yet intuitive detective Steve Keller in the iconic TV series The Streets of San Francisco. In many ways, The Streets of San Francisco was your standard crime drama, but the dynamic between the sage veteran detective Mike Stone played by the singular and authentic thespian Karl Malden and a raw and up-and-coming Michael Douglas made the show a classic cops-and-robbers favorite. And an honorable mention in the show would have to be Michael Douglas’ hair! Wow! The young actor went on to pay a lot of bills with that do. And let us not forget, the guy still has a great head of hair to this very day!

How about you? Any Michael Douglas roles that stand out? Please share!