10 Underrated Movies from 1998

by Patrick Bromley

Some movies I want more people to like more!

I've been doing a massive 1998 rewatch in the run up to F This Movie Fest this weekend, and in the process discovered or re-discovered a bunch of movies I really like that either don't get talked about much these days or are written off as just being plain bad. While there were more than just 10 movies I really liked this past month, I thought I'd highlight some that deserve better than their reputations. Enjoy!

1. Pecker (dir. John Waters)

This got a huge surprise bump during this month's rewatch. I remember seeing it in 1998 and thinking it was pretty mid-to-lower-tier John Waters and that maybe working with New Line had defanged him a little. I don't think I realized at that time that New Line had produced or distributed many of his movies and couldn't be blamed for tempering his sensibilities. What I found this time was not just a satire of the art world but a surprisingly sweet and incredibly charming ode to the people of Baltimore and to anyone who has ever felt like a misfit. That's not unusual for Waters, whose every film celebrates the outsiders, but here it's done with such gentle affection (as gentle as a movie with a recurring joke about teabagging can be) that I was completely won over by it. Edward Furlong gives his best performance this side of Judgment Day and the ensemble really shines, though none as much as Martha Plimpton as Pecker's older sister, an honorary gay man.

2. Mighty Joe Young (dir. Ron Underwood)

One of a handful of first time watches for me this 1998 month, Ron Underwood's remake of the 1949 King Kong spinoff Mighty Joe Young is a totally serviceable adventure movie bolstered by incredible ape effects and a super dialed-in early Charlize Theron performance from that late-'90s period where she was able to sell any material (see also: Trial & Error, The Devil's Advocate). The action is decent even though the bad guys are kind of lame and the final set piece, in which Joe finds himself at a carnival, isn't as cool as what came before, but there's enough here that works that this should be considered one of the better live-action Disney movies of this period. 

3. Six Days Seven Nights (dir. Ivan Reitman)

The movie that inspired this list. When I saw this movie on VHS back in the late '90s (I skipped it in theaters, making me part of the problem), I thought it was just ok and not remarkable enough to stand out in the crowded summer of 1998. Revisiting it after Ivan Reitman passed a few years ago (and then again last week), I think it's kind of a great example of its very specific subgenre: the romcom by way of an adventure movie set in a gorgeous tropical locale. Is it Romancing the Stone? No, but it didn't deserve to be buried by the tabloid press more concerned with star Anne Heche's (RIP) sexuality than with whether or not the movie is any good. It is. Harrison Ford seems to be enjoying himself as a grouchy pilot and has real chemistry with Heche as the frazzled woman who hires him for a flight only to find herself stranded with him on an island alone -- or so they think. When he's on his game, Reitman is good at balancing genres and tones, mostly succeeding here. The photography is beautiful, the stars appealing, the screenplay just funny and exciting enough to deliver what we want from a movie like this. This most recent viewing confirmed that I'm going to become a drum-beater for Six Days Seven Nights.

4. Permanent Midnight (dir. David Veloz)

I remember dragging Doug and our friend Tony to the Piper's Alley theater in downtown Chicago to see this one because it co-starred Janeane Garofalo, on whom I was nursing my biggest-ever celebrity crush at the time. I was also a fan of Ben Stiller during this period because I was a huge Ben Stiller Show guy and he was choosing really offbeat and interesting projects as an actor, a trend that would more or less end after a monster 1998 that included this movie as well as Your Friends and Neighbors, Zero Effect, and There's Something About Mary, the film that brought him the mainstream success (well, that and Meet the Parents in 2000) that would end his cool run. In Permanent Midnight, he plays real-life writer and real-life heroin addict Jerry Stahl, who managed to turn out scripts for shit like ALF while high on junk. I'm not a big addiction movie guy -- that's Adam Riske's department -- but the movie finds both dark comedy and genuine pathos in the nightmare that was Stahl's drug habit. I miss the Ben Stiller of the 1990s.

5. Black Dog (dir. Kevin Hooks)

This came up on a recent podcast as part of Adam Riske's "junk action" 1998 double (alongside Firestorm), and it totally is junk action but in the best possible way. Patrick Swayze elevates an otherwise goofy truck driver movie in which he plays an ex-con who has to transport a bunch of illegal guns in order to save his house, all while holding off the FBI and a criminal named Red (an unhinged Meat Loaf), whose crew is attempting to hijack the load. Director Kevin Hooks (Passenger 57) knows how to stage solid action and Swayze lends a ton of gravitas to a movie that would otherwise plummet off a cliff. Movies like this used to know exactly how to deliver on what we wanted from them.

6. Two Girls and a Guy (dir. James Toback)

In 1998, a movie about three people talking and arguing in an apartment seemed somewhat revolutionary, a clear descendant of the John Cassavetes approach to filmmaking. In 2025, it would be just another COVID movie. Robert Downey Jr., a decade away from Tony Stark and mostly written off at this point as a trainwreck and an addict, gives a tour de force performance as an actor and narcissist who gets caught having a relationship with two women (Heather Graham and Natasha Gregson Wagner) at the same time. The film, which feels heavily improvised both when it is and when it isn't, has a lot to say about love, sex, and relationships, but even more to say about lying and gaslighting. Make no mistake, director James Toback is a scumbag, but he knows his way around lying and gaslighting. This was on my list of favorites back in 1998, and while it wouldn't be anymore it's still a really good version of exactly the movie it wants to be.

7. Stepmom (dir. Chris Columbus)

I hadn't seen this since opening weekend 1998 and, to be honest, haven't thought of it much in the years since because I didn't really care for it back then. I wanted to revisit it out of respect for Adam Riske because Chris Columbus is one of his guys (#twofistsofColumbus) and was surprised to find a movie that's much more mature and nuanced than I remembered. Yes, there's some sitcom hijinks in which OG mom Susan Sarandon tries to undermine new stepmom Julia Roberts and people definitely sing into hairbrushes and Jena Malone's daughter character is basically the worst, but there are also some very real observations about family relationships and about -- of all things -- facing sickness and death with dignity. I shouldn't be totally surprised; Columbus also made Mrs. Doubtfire, a sporadically smart movie about marriage and divorce when it's not about the stupid old lady makeup. Stepmom is kind of like that: a movie that gets out of its own way often enough to work well as an intelligent family drama.

8. Caught Up (dir. Darin Scott)

If you're a Patreon subscriber, you know I've been championing this movie for a while. This modern day blaxploitation film stars the great Bokeem Woodbine (who also more or less stole The Big Hit this same year) as a convict who's trying to go straight until a psychic woman -- the spitting image of his girlfriend (Cynda Williams in one of the great "Holy shit, who is that" turns) -- enters his life and wreaks havoc. There's just enough mystical shit in this to make it weird, with a story that's almost impossible to predict and a surprise cameo at the end both pays off making it to the end of the movie and certifies it as a classic, albeit one that not enough people have seen. This was the directorial debut of screenwriter and producer Darin Scott, a genre legend (with titles like Tales from the Hood, Fear of a Black Hat, and Menace II Society among his credits) who should have gotten more turns behind the camera.

9. The Spanish Prisoner (dir. David Mamet)

JB has written about this one in the past. Its modern reputation is for being lesser-known (or even "lesser") David Mamet, who wrote and directed it, but that's underselling just how good it is. Campbell Scott plays an everyman who invents a new process (called only "The Process") and then meets Steve Martin, very good in a dramatic turn and playing a guy who fucks everything up. I'm a sucker for a con artist movie and few people make them better than Mamet. Special attention should be paid to Carter Burwell's effectively moody score and to the performance of Mamet's wife Rebecca Pidgeon, whose performance JB does not like but who, for me, is the key to unlocking the joy of the film. Her line deliveries are so offbeat and her affect so impenetrable that it's impossible to know who she is or what she's after, turning The Spanish Prisoner into a guessing game inside of a guessing game. 

10. City of Angels (dir. Brad Silberling)

Another movie I like more every time I see it. My favorite actor of all time Nicolas Cage makes for a profoundly weird romantic lead as an angel who falls in love with surgeon Meg Ryan and decides to become human to be with her. I'm a huge fan of writer/director Brad Silberling's Grief Trilogy (which also includes Casper and Moonlight Mile), and this one is the most confident and offbeat of the three. Not knowing much about the director when I saw this as just another tearjerker in 1998, I now appreciate it a lot more as a meditation on the loss of Silberling's partner Rebecca Schaeffer, who was murdered in 1989. I like when Nic Cage manages to smuggle lots of weirdness into his mainstream Hollywood movies, which he does here. Plus, I'm not sure he's ever looked hotter in a movie. Somehow it took me until this most recent viewing to notice the cameos from Amy Brennaman (Silberling's current wife) and Michael Mann. I still haven't seen Wings of Desire, the Wim Wenders film on which this one is based, but I've now seen City of Angels so many times that I probably never need to.*

*That's a joke