11 '90s Boyfriends From '90s Movies & TV Shows Who Were Absolutely Terrible

The ‘90s, darling little decade that it was, gave us a lot of complicated, albeit undeniably charming dudes to pine over: There was Jordan Catalano (Jared Leto) from My So-Called Life, Patrick (Heath Ledger) from 10 Things I Hate About You, Will (Will Smith) from The Fresh Prince of Bel-Air, Zack Morris (Mark-Paul Gosselaar) from Saved by the Bell, Jesse Katsopolis (John Stamos) from Full House, and so on. But do you know what that decade of TV and cinema also gave us? So many terribly undateable '90s fictional boyfriends, that’s what. It's as the old saying goes: For every Patrick Verona who serenades Kat Stratford with "Can't Take My Eyes Off Of You," there are at least a dozen trolly suitors lining up to date the four main characters on Sex and the City.

Will I name names? Psh, you better believe I'm about to name names. I spent some time rifling through the '90s pop culture archives and picked some of my favorite least favorite '90s boyfriend characters. The boyfriend characters who really, really stink. The boyfriend characters I love to hate the most.

The following annoying and/or creepy and/or awful and/or frustrating characters are some of the most undatable beaus to appear on both the big and small screens. What's the opposite of a crush? Because that's what I have on these guys.

1. Brock Hudson (Matthew Lillard) From She’s All That

Listen, I dig revisiting old Real World episodes as much as the next ‘90s kid, but there is a limit. And that limit is watching a dude scream along with reruns of his own season of the Real World.

2. Big (Chris Noth) From Sex And The City


3. Berger (Ron Livingston) From Sex And The City

Before there was ghosting, there was Post-It noting. (Yeah, yeah, I know “The Post-It Always Sticks Twice” aired in the ‘00s, but I’m bending the rules for this one. Sorry, but I couldn’t not include Berger and his Post-It move.)

4. James Hurley (James Marshall) From Twin Peaks

He’s not terrible-terrible, but he is so pouty. Like, exhaustingly pouty. Also? After this leather jacket-wearing bore’s quasi-girlfriend, Laura, is murdered, he falls for her best friend and her cousin. Sure, we all mourn in our own way, but dating your deceased secret ex's closest pal and pining after her doppelgänger cousin? Those are some pretty transparent moves, bro.

5. Jim (Anthony Michael Hall) From Edward Scissorhands

This mean and jealous and crazy-aggro dude gets his just des-sciss-erts.

6. Sebastian (Ryan Phillippe) From Cruel Intentions

Before he — spoiler! — dies a hero, Sebastian is a real deviant goblin who will do whatever it takes (i.e, threaten blackmail a bajillion times) to get what he wants.

7. Crazy Joe Davola (Peter Crombie) From Seinfeld

I mean.

8. Cal (Billy Zane) From Titanic

Heart of the Ocean? More like Fart of the Ocean, amirite?

9. Riley Finn (Marc Blucas) From Buffy the Vampire Slayer

Is he the worst character to ever exist in the Buffyverse? No. Is he a wildly annoying boyfriend? You better believe it. Every time I think about that whole “I wish my Slayer girlfriend would pay more attention to me, so I’m going to go let vampires feed on me” stunt he pulled, my face crumples up like one of those crinkly popcorn blouses.

10. Spike (James Marsters) From Buffy the Vampire Slayer

One second, this vampire is a chill good guy who the Scoobies can trust. The next, he’s an evil monster who tries to force himself on Buffy (Sarah Michelle Gellar). No, thanks!

11. Billy (Skeet Ulrich) From Scream

Sidney’s (Neve Campbell) boyfriend is — spoiler alert! — a literal serial killer. He is actually the worst.

Images: Miramax Films; caseyafflecks, infinite-pleasure, twinpeaksgifs, sempeternal, graysondick, agameofmiserables, cordysummers, coalitiongirl, hxllosidney/tumblr; HBO