Cliff Pantone (Jesse Bradford): Bring It On (2000)

Every time I watch this movie, I just really want to be friends with a guy like Cliff. He is so funny, and smart, and in a band? Okay sure, I would totally fall for a guy like this. I think a lot of it has to do with his quirky persona, but in all actuality, he wrote the girl a song to make her feel better about her cheer issues (that sounds silly, but you know what I mean) and was really supportive of his sister, trying to get her to branch out and join the team. Although I will admit that he could have been a bit more understanding when Torrance’s boyfriend at college came back, and she broke up with him soon after. Maybe that’s just me, though. I don’t know, I still really like Cliff’s character, but then again, her relationship with him isn’t really one of the most pivotal conflicts within the film to begin with.
Character Grade: 8.5/10
Rob Gordon (John Cusack): High Fidelity (2000)

Oh hello John Cusack, nice to see you on our list again. Now, maybe not as many people would consider Rob Gordon a “teenage” heartthrob, but really, he was created to be a character for you to love, so just bear with me on this one. All in all, I love the fact that he makes lists to get over things, because really, I do too. And he really tries to figure out his life and move on once Laura dumps him. At the same time, however, trying to justify his cheating and actions while she was pregnant is a little, well, douchey. Musical snobbery is never good either, especially when it comes to your friends. Didn’t he almost not let one of his close co-workers play at an event? Don’t you trust your friends, Rob? I don’t know, this one was kind of mixed, and I think I would have to watch it again to really decide on Rob.
Character Grade: 4/10
Ryan Woodman (Shane West): Whatever It Takes (2000)

Like High Fidelity, I don’t really remember this movie a lot, just the major stuff. And as much as I love Shane West and wish his character in A Walk to Remember could have made the timeframe cut to be on here, sadly we have to go with a slightly less-likable character for him. Now, Ryan Woodman is definitely loveable, I mean he plays the accordion for goodness sake! And he also ends up with his oldest friend (as it should be) but boy does it take a long windy path to get there. And why was he so obsessed with the popular girl who was just awful when there were so many other perfectly good girls? Why wouldn’t he protect his best lady friend from the greasy James Franco if he knew what a skeeze he was? Why would he go to prom with a girl that he didn’t really like (even if she was acting like a crazy person until he was)? Was having that cool status really that important to him? Oh but in the end he was good to his best friend and they really did belong together, I just think he made a mess of things up to that point, and shouldn’t have been so oblivious to her feelings and all that. Though I know, sometimes that happens, especially with someone you know so well.
Character Grade: 5/10
Berke Landers (Ben Foster): Get Over It (2001)

It seems like until I made my friends watch this with me, pretty much nobody I knew had seen this movie. To my sister, however, it was a classic, and Martin Short is just hilarious in it! Anyways, I think I may be biased because I really like Ben Foster, but besides that, Berke wasn’t so bad. Arguably, he really could have gotten over Allison in a much less painful way, and could have been a little more mature about it, rather than trying to weasel his way back into her life when she had another boyfriend. He did, however, indirectly show her what a tool her new boyfriend was, and did realize how good his best friend’s little sister was. Now I’m torn on the whole, “But you’re Felix’s little sister” issue, I mean I can see why he wouldn’t want to hurt his best friend, but also why wouldn’t he be willing to give it a shot and talk to his friend about it? I don’t know, he still seemed like an okay guy. A little odd, but pretty good.
Character Grade: 6.5/10
Derek Reynolds (Sean Patrick Thomas): Save the Last Dance (2001)

Now, besides all that “gangster friends” business perpetuating the African American stereotype, I really think that Derek Reynolds was a great fictional boyfriend to have, even though I can’t remember ever wanting him. Why was he so great? Well, he was pretty smart for one thing, getting into a good college, and taught a stiff ballerina how to be somewhat hip-hop (though how “street” can Julia Stiles really be? Not all that impressive but that’s not what we are talking about). Also, he never let those issues others had about interracial couples get to him, even when they got to his lady-love. Plus he got out of the gang and was big support to Sara’s shaking dancing dreams. All in all, Derek was really nice guy, and had a good head on his shoulders next to some less-than amiable others.
Character Grade: 9/10
It appears that like the 1990s, the 2000s also had some ups and downs. After the whole things, however, and considering all the character flaws, despite the fact that some other guys from each decade might have a better "grade" overall, I still can't help but fall for a couple certain fellows. That being said, my one true "boyfriend" from each decade are as follows:
1980s: Jake Ryan, 1990s: Preston Myers, 2000s: Cliff Pantone
And since that is that for this adventure in examination, what do you think? Was I too hard on anyone, or too easy on someone else? Was there one specific decade of teenage hunk that you liked more than the others? How about anyone that I missed in my assessments?






























