1991 is a landmark Bruce Willis year for me as a fan. Not only do we get the insane vanity project that is Hudson Hawk (more on that soon) but we also get one of my absolute favorite Willis vehicles, The Last Boy Scout (more on that next time). But first-

In Mortal Thoughts, Bruce plays an alcoholic, abusive husband to Glenne Headly. His real life wife at the time, Demi Moore, is the films lead, and the movie is told from her POV as she is interrogated by two detectives working Willis’ murder. That’s right! Bruce dies early on, so it’s a small but crucial role where he gets to go full asshole.

The good news? Bruce is a very believable asshole. The bad news? The movie is melodramatic to the max and filled with one note caricatures and performances (yes, that unfortunately includes Bruno). The movie tries to play itself off as a mystery with its flashback infused narrative, but every idea is so half baked and every performance is so over acted that any dramatic tension is stripped away immediately. According to its Wikipedia page, the film had numerous production problems, including losing the director one week into production as well as an incomplete script, which led to many scenes being improvised, a fact that is painfully obvious throughout. In fact, it feels like most of Bruce’s scenes were one and done takes, as his performance feels like it belongs in an after school special rather than a major motion picture.

It’s also the first time in his short (at this point) career that his choice to make this movie doesn’t really make sense on paper either. There’s no acclaimed director or screenwriter attached. Aside from Demi and Glenne, there really isn’t a crazy cast in this one either (Harvey Keitel plays one of the cops interrogating Demi, but he’s only in about 10 mins of the movie and his and Bruce’s character never interact). Part of me thinks that Bruce Willis: Movie Star is starting to overtake Bruce Wills: Actor at this point. Which makes sense really, Die Hard immediately put him in the big leagues of Hollywood, so why not make movies that specifically showcase yourself and your talents? In the case of Mortal Thoughts, it’s a chance to work with his wife (which is good press) but it also gives him a chance to get dark and heavy with an intense, unlikable character.

All for naught, though, as Mortal Thoughts was another critical and box office disappointment, grossing only $18 million domestically.

No matter! Bruce Willis: Movie Star had another trick up his sleeve, and this time he knew, he just knew he was gonna blow the competition out of the water.

Since Bruce was starting to use his Movie Star clout, he knew he had to make a big, entertaining movie that would cement his position as one of the biggest stars in Hollywood. Bruno had actually been cooking up this idea for a while (our man even gets a story credit here), so he brought on one of the writers of Die Hard to co write, a hot up and coming director (Michael Lehmann, still riding high off Heathers) and Hollywood giant Joel Silver (Die Hard 1 & 2, Lethal Weapon 1-4) to produce.

I LOVE this movie. A goofball action comedy musical (!) that follows Hudson Hawk, a famed cat burglar (who is a fiend for cappuccinos) that gets roped into stealing multiple works of Leonardo Da Vinci immediately after he’s released from prison. To say that hijinks ensue simply does not do this movie justice.

The film is both a spoof and a love letter to action comedies that I don’t think audiences were ready for at the time (the similarly meta Last Action Hero would also prove to be a misunderstood disappointment just two years later). To be fair though, Hudson Hawk swings pretty broad, and more often than not the jokes fall flat, but somehow over time that has become part of the films charm. And the jokes that do work are usually pretty fucking weird, another sign that tells me that audiences just weren’t ready for this kind of madness from an action star.

Speaking of action, the action featured isn’t particularly great, and more often than not follows the rules of Looney Tunes rather than reality, but again, that’s kind of the point.

Anyway, there are so many choices made in this movie. Heists timed to musical numbers performed by Willis and Danny Aiello (!), naming goons after chocolate bars, David Caruso. It’s a roller coaster of WTF, and it’s all thanks to the vanity of Bruce Willis. Bruce was determined to make a crowd pleasing action comedy, so he really threw everything and the kitchen sink at this movie.

It really is so insane to me that this is the film that Willis wanted to make. It does kind of make sense though. He’s got his bona fides in both action and comedy at this point, so why not mix it together? And man, Bruce is having a blast here. He gives 110%, whether its mugging to the camera, spewing out one liners or giving off the coolest and most badass vibes on the planet Earth, he goes for it.

The rest of the cast is just as game if not entirely suited for the material. Danny Aiello goes with the flow, James Coburn gets the joke completely and Andie MacDowell tries her best. But its Sandra Bernhard and Richard Grant that really go for broke as the billionaire villains playing their own version of The Da Vinci Code.

The production of this film was as chaotic as the film itself, as James Greenberg profiled for The New York Times. As the budget soared, so did expectations. The film opened in late May of 1991, a prime blockbuster release date, only to come in third place behind the first weekend of Kurt Russell’s fireman drama Backdraft and the second weekend of What About Bob? starring Bill Murray. When all was said and done, Hudson Hawk grossed $17 million off a reported $65 million budget. It was the second mega budget flop in as many years for Bruce. Oof.

Alas, time has been kind to Hudson Hawk, as film nerds like me have come to embrace the weirdness of the film and its effort to try something new. It’s choices like this that make Bruce Willis fascinating to me. This was his first big time Hollywood swing standing on own, and he went all in. Granted, he may have missed, but man what a swing.