Last we left Ol’ Bruno, he had just starred in Blind Date, a romantic comedy that turned out to be a modest hit in 1987, as well as Sunset, a 1920s Hollywood whodunnit that crashed and burned on arrival in early 1988.

And then came Die Hard.

As I’ve stated previously, I won’t be reviewing or talking about Die Hard as a film, but it would be foolish not to talk about the immediate effect that movie had on his career.

First off, it’s important to remember that up until Die Hard, Willis was mostly known for his comedic work, so when he signed on to play a tough and street wise New York cop in an action movie from the director of Predator, people weren’t exactly convinced it could work.

But then the movie came out.

Die Hard grossed $83 million domestically and over $141 million worldwide and of course time has assessed that it is indeed one of the greatest, if not the greatest, action film of all time. Seemingly overnight, Bruce had turned into a superstar.

So now that he had his action bonafides and proved his comedic chops a few times over, Bruce decided to go that movie star route, and star in the film In Country.

Released during awards season in 1989, In Country follows recent High School graduate Samantha as she tries to learn more about her father, who died in Vietnam, by asking her uncle Emmet (Willis), who has his own demons from the war to deal with.

Directed by acclaimed director Norman Jewison (In The Heat of the Night, Moonstruck), In Country was one of multiple films in the late 80s that tackled the fallout of the Vietnam War. Films like Platoon (which won Best Picture at the Oscars in 1987), Born on the Fourth of July and Casualties of War. Unfortunately, In Country is not one of the better films on the subject. The film is hokey and sappy in the extreme, and features a lead performance from young actress Emily Lloyd that borders on parody. The film has the best of intentions, and I feel like everyone involved really wanted to shed light on the damage done to all the young men who fought and gave their lives, but damn….what we got is just a surface level drama filled with characters better suited for The Andy Griffin Show.

But, once again, our boy Bruce comes out unscathed. In fact, Bruno is flat out great here.

Nobody wears regret better than Willis. With one look and a single sigh, we feel and understand the lifetime of hurt his character Emmet has gone through. The film lets Bruce run a gamut of emotions from sad and quiet to drunkenly losing his shit during a thunderstorm ,and despite the rest of the film around him, Bruce’s performance always rings true.

I think it’s important to reiterate at this moment that even though this movie as a whole doesn’t work, it makes a lot of sense as to why Bruce chose it. Allow me to explain.

So Die Hard comes out, and it’s huge. Bruce is huge too and he can essentially do what he wants, and on paper, In Country seems like a good bet. Directed by seven time Academy Award nominee Jewison and written by the Academy Award winning writer of Dog Day Afternoon and Cool Hand Luke, In Country had legit pedigree behind it. Bruce was trying to be a real deal actor, and In Country was his chance to prove it.

Of course, it didn’t exactly work out. In Country grossed a paltry $3 million and was largely ignored by critics too, but they at least gave what little praise they had to Willis’ performance. Also, Bruce did garner a Golden Globe nomination for his work, which isn’t a bad consolation prize.

Anyway, 1989 wasn’t all bad for Bruce. He had a giant hit with Look Who’s Talking, where he voiced the inner monologue of a baby being raised by John Travolta and Kirstie Alley (yes this movie is real). The film grossed $140 million domestically and almost $300 million worldwide, Willis’ biggest hit to date at the time.

1990 started out well too, with Die Hard 2: Die Harder outgrossing the original with $117 million domestically and $240 million worldwide. Look Who’s Talking Too also premiered in 1990, but underwhelmed with $47 million in the U.S.

Which brings us to….

Hoo Boy. Talk about a good old fashioned Hollywood disaster. The Bonfire of the Vanities is one of the biggest and most notorious flops of the 90s.

But first, a little context. The movie was based on a very successful book, and all signs pointed to this being a darkly comic, thought provoking adult drama perfectly suited for awards season and all the star power the box office could handle.

Director Brian De Palma (Scarface, The Untouchables, Carrie, Mission: Impossible) brought his auteur status with him as well as stars Tom Hanks, Melanie Griffith, Bruce and a treasure chest full of recognizable character actors throughout. Again, Hollywood was convinced they had a monster hit on their hands.

But shit, man. Everything about this flick is wrong. I think this is the first mainstream movie I’ve ever seen where just about every major character is miscast. Tom Hanks is just wrong as the lead, a sleazy Wall Street tycoon who finds himself in a tough spot after his mistress hits a black teenager with his car after he and another kid tried to mug them. I truly believe Tom is capable of playing a character like this. Honestly, I would love to see him sink his teeth into playing an asshole such as this because people really forget what a truly gifted actor he is. Here, however, he’s too young and just too innocent looking. He wears a set of fake teeth that are cigarette stained and it just makes Hanks look ridiculous rather than disgusting, which I think was what they were going for.

The tone of this movie is all kinds of wrong too. It so badly wants to be a scathing satire on upper class foolishness, but the comedy is often sitcom level bad. There is no dramatic momentum either, because even though Hanks’ character is getting wrongly accused of a crime he didn’t commit, you kind of don’t care because the character, quite simply, sucks.

Melanie Griffith, an actress who has been much better in many movies before and since, provides the films sole laugh with the line “You know I’m a sucker for a soft dick, Sherman.” It’s an awkward line in an awkward scene in a very awkward movie, but I must admit it’s one that will stay with me forever.

As for Bruce, well, he does what he can, but even he feels like a bad fit as an alcoholic reporter in desperate need of a good story. Truthfully, he’s not very good here either, but it’s not really his fault. The Bonfire of the Vanities is an example of a production that made every bad choice that could be made. A quick look at the films Wikipedia page shows just how tumultuous the making of the film was.

The Bonfire of the Vanities was released in December 1990 to scathing reviews and poor box office. Grossing $15 million off a $47 million budget, Bonfire was a certified Hollywood disaster.

But once again, you can see how this seemed like a good career move, at least on paper. Brian De Palma was one of the most acclaimed filmmakers of the 70s and 80s, and almost everyone in the cast was an A list celebrity, at least at the time. The good news is that Bruce didn’t have to take all the blame here, but it was the beginning of a four year drought for Bruce, filled with critical and/or box office disappointments.