He first captured the world’s attention in the landmark television series Moonlighting. Since then, he’s gone on to do a lot of variations on the theme of both that and the No. 1 film on this list. He’s always just right as the wisecracking everyman, and at least a third of his career could be described as Die Hard on a….
For example, The Last Boy Scout (1991) was a breath of fresh air that poked fun at the genre that promoted him into the stratosphere and RED (2010) still stands up to almost everything on this list. But look no further than these five for the cream of his crop.

Die Hard (1988)
He’s fighting back against the behest of the police/FBI, save first man on the scene Sgt. Al Powell (Reginald VelJohnson), who can’t offer much more than empathy and the ingredients of a Twinkie. So McClane’s very much the modern-day twist on an old cowboy, taking his cues from Roy Rogers while spouting such seminal lines as “Yippee-ki-yay, mutherfucker!” and “Geronimo!”
The sharp script fleshes out all the characters, even poor authority figures like the Deputy Police Chief (Paul Gleason) get zingers about needing more FBI guys, so it takes a lot of John to come on top. It’s a propensity that continues to pay off for Willis, and not just with the litany of Die Hard movies that have come out in the years since this blockbuster.
Moonlighting (1985-1989)
Those who were around to watch the show in its original run remember how often it was in reruns due to behind-the-scenes drama. But the legacy of Moonlighting, which began in 1985 and ran for five seasons, was so much more than that. It didn’t just knock down the fourth wall, it took a pick ax to it. It made Shakespeare and filming in black-and-white cool again with groundbreaking episodes such as “Atomic Shakespeare” and “The Dream Sequence Always Rings Twice” respectively. And David Addison didn’t just provide a blueprint for detective shows, you can find pieces of him in virtually every genre across the TV landscape.
Unbreakable (2000)
We’re spellbound watching David come to grips with that discovery and attempting to figure out how to make best use of his talents so he can help as much of mankind as possible in true good-guy fashion. But that final denouement with Elijah Price — a fixture in all such battles in the comic universe — is downright spine-tingling. Can’t wait for 2019’s Glass, which marries Shyamalan’s own career rejuvenator Split (2016) with Unbreakable.
Pulp Fiction (1994)
It gave us a chance to see Willis play a bit of pretty much every role included on this list over the course of his screen time. He’s the tough guy, he’s a lovable rogue capable of sweet talk, he’s down on his luck and he’s got to work his way out of an impossible situation. Yet when all of it came together, it felt like something completely new.
12 Monkeys (1995)
Is he in the mental institution because he belongs there or because it’s safer to have him there? It’s a testament to Willis and a plot that keeps turning in on itself that we wonder about that for long stretches, it gives the movie more depth and raises it above more traditional sci-fi fare. And it’s equally enjoyable to find him being dragged almost kicking and screaming into trying to save the world. It’s so un-Bruce Willis.
Paige reviews classic television and movies for Sibling Cinema. They’re currently in the midst of a rewatch blog for the complete run of The X-Files.