21 Toxic Guys From '00s Movies We Loved To Hate

Movies of the early 2000s gave us many things: best friends, enemies, the not-so-secret hope that we were actually secret princesses (thanks, Garry Marshall), and, of course, swoon-worthy girls and guys we all wanted to date. Personally, movies gave me countless fake boyfriends to lust over, like Cliff from Bring It On or Emmett from Legally Blondemen who were kind, smart, and, best of all, romantics at heart. But, just as early '00s movies gave us all dream boyfriends, they also gave us boyfriends of nightmares — male characters who were self-absorbed, demanding, demeaning, and just all around toxic. These 21 toxic guys from early '00s movies we loved to hate and hated to love, all at the same time, are just a few examples of the scum we had to deal with.

What makes a man toxic? Well, in the early '00s, the term "toxic" was pretty much defined by Britney Spears in her iconic single. A toxic guy was addictive, dangerous, bad for you, but irresistible at the same time. Now, when we talk about toxic people, we talk about people who bring out awful traits in others, who encourage negativity and foster tense, hostile environments. No matter how you define toxic, I think you'll agree that these 21 men from early '00s movies certainly fit the bill.

1. Warner — 'Legally Blonde'

Warner was the worst — a guy who dumped his sweet, loving girlfriend because he underestimated her and wanted to be an ~elite~ lawyer. NEXT.


2. Aaron — 'Bring It On'

Aaron was another early '00s movie boyfriend who got an F in supporting your significant other. When he told Torrance that she wasn't "Captain material," he tore down her confidence and earned himself a place in the Toxic movie dude hall of fame.

Universal Pictures

3. Josh Bryant — 'The Princess Diaries'

The Princess Diaries was all about embracing beauty on the inside, but that doesn't mean that everybody actually is beautiful on the inside. Case in point: Josh Bryant, the drool-worthy popular boy who also happened to be a fame-seeking jerk. Boy, bye.

Walt Disney Pictures

4. Christian Thompson — 'The Devil Wears Prada'

Hot shot photographer Christian Thompson wasn't the most toxic influence in Andy's life, but he definitely didn't help matters. He was sneakily toxic, all seductive and sweet, but poisonous on the inside.

20th Century Fox

5. Justin — 'She's The Man'

Justin's most toxic sin: thinking boys were better than girls. Sorry, dude, but you're on your own.

DreamWorks Pictures

6. Harry — 'Love Actually'

Anyone who breaks Emma Thompson's heart is toxic. Period.

Universal Pictures

7. Hugo — 'O'

I don't think it gets any more toxic than a guy who tricked his supposed best friend into murdering the love of his life.


8. Harry Osborn — 'Spider-Man 2 & 3'

Even before Harry Osborn became the next Green Goblin, he was a pretty toxic friend, cozying up to Peter's girl, MJ, while he was off fighting crime. He also felt the need to infect everyone with his bad mood, which is just not healthy for anyone.

Columbia Pictures

9. Cooper — 'Center Stage'

Cooper slept with a student, and then was mean about it, almost costing other students their roles on stage. Not cool, man.

Columbia Pictures

10. Michael — 'Honey'

Michael encouraged Honey to ditch her best friend's birthday and then proceeded to try to end her choreography career when she refused to sleep with him. Forget Toxic, Michael was plain rotten.

Universal Pictures

11. Dylan — 'Crossroads'

Dylan barely appears on screen in Crossroads, but man was he a toxic jerk. Dylan was engaged to Kit and was the jerk who slept with Mimi, impregnated her, and then disappeared. At least one good thing came out of Dylan's toxic behavior: he inadvertently brought Kit, Mimi, and Lucy back together as BFFs.

12. John Tucker — 'John Tucker Must Die'

Once a cheater, always a cheater. John Tucker's cheating ways created a high school environment where women hated each other because of his actions. Any guy who pits women against women is toxic in my book.

20th Century Fox

13. Aaron Samuels — 'Mean Girls'

Aaron Samuels was either a totally toxic guy or a complete idiot for not realizing how Regina and Cady were using him/fighting over him. Also, I know she had redeeming qualities, but what exaclty did Aaron see in Regina other than her looks and sex? Either he knew exactly what was happening and didn't care (TOXIC) or his idiocy extended way beyond Calculus.

Paramount Pictures

14. Nate — 'The Devil Wears Prada'

Nate's toxicity level has long been the subject of debate. Is he just a good guy trying to show his girlfriend she's changing for the worse, or is he a controlling boyfriend who doesn't support Andy in her work and refuses to see his significant other grow? I'm not sure I know the answer, but the fact that we even have to ask should be enough to raise some eyebrows.

20th Century Fox

15. Russell Hammond — 'Almost Famous'

Russell Hammond may have been a Golden God, but he was also kind of a trash human being. Toxic level: hazardous.

DreamWorks Pictures

16. Frank Abagnale Jr. — 'Catch Me If You Can'

As much as it pains me to put Frank Abagnale Jr. on this list, he was a conman who almost tricked sweet nurse Brenda Strong into marrying him. He also asked her to become a fugitive for him without really thinking it through.

DreamWorks Pictures

17. Jasper — 'The Holiday'

What's almost as bad as cheating on Emma Thompson (Love Actually)? Cheating on Kate Winslet. In The Holiday, Jasper was a classic narcissist who needed love from all women, even while he was engaged.

Sony Pictures

18. Daniel Cleaver — 'Bridget Jones's Diary'

You don't even have to know what Daniel Cleaver did in Bridget Jones's Diary to know that he's toxic. That hair alone speaks volumes.

Miramax Films

19. Eric Knox — 'Charlie's Angels'

Plotting to murder the woman you just slept with is considered toxic, right?

Columbia Pictures

20. Jim Danvers — 'In Her Shoes'

Sleeping with a woman and then cheating on her with her sister just because she answers the door is pretty much the definition of sleaze.

20th Century Fox

21. Neal — 'Uptown Girls'

Neal dumped Molly after he got all his inspiration from her — "Sheets of Egyptian Cotton," anybody? Plus, he wasn't nearly as cool as he thought he was. Yes, he redeemed himself in the end, but, he still caused a lot of hurt.