the best ever

***this monday, as a service from the kind gentleman of, the champ has decided to rank the three best romantic comedies of all-time the last 20 years. enjoy***

3. chasing amy

premise: a comic-book writer (ben affleck) befriends and falls in love with a fellow comic book writer (joey lauren adams)…who happens to be a lesbian. hilarity, pain, tremendous cussing, and unfortunate ho-yay behavior ensue.

reasons for making the cut:

—easily the best movie kevin smith ever made. this isn’t even remotely debatable

—contained quite possibly the funniest token black character ever on screen, in dwight ewell’s “hooper x”, a fellow comic book writer, who also happens to be extremely violent, extremely militant, and extremely gay. omar would have been proud

—introduced “finger-cuffs” to my general lexicon, a term i still use with glee at least thrice daily

—perfectly captures a typical male’s queasy uneasiness when forced to confront his woman’s, ummmm, “eclectic” sexual past, and how hard it is for us to let that go.

—would have rated higher on this list if not for the ending, which is so inconceivably and shockingly bad that i refuse to even talk about it

2. boomerang

for black people those willing to put saccharin garbage such as “the best man” and “brown sugar” ahead of “boomerang” when ranking romantic comedies, consider the following…

—talent-wise, when you consider eddie murphy, martin lawrence, david alan grier, and john witherspoon this movie contained four (five if you count grace jones’s vagina) comedic legends in their absolute prime, as well as a before her prime halle berry, a still barely unattractive tisha campbell (before she made the leap to “completely unattractive”), lela rochon’s feet, and a surprisingly milfy eartha kitt. wow.

—the infamous thanksgiving dinner, where witherspoon’s “mr. jackson” introduced the world to the concept of “coordination” as well as “pop that pu–y!!!“, is easily one of the five funniest movie scenes of all-time

—was the best of the numerous roles robin givens seemed to land where she played herself evil, conniving, manipulative bitches

1. high fidelity

maybe this movie gets top billing solely because it’s the movie that inspired me to start making lists for everything. maybe it’s number one because i see so much of myself in john cusack’s rob gordon, and it perfectly illustrates that late 20’s “i guess i should settle down with her cause i guess at this age it’s the right thing to doi guess” angst…a phenomenon i’m currently experiencing i completely understand. maybe i just want to sleep with meet lisa bonet. who knows. i will say that, despite its basically all-white cast, it’s quite possibly the “blackest” relationship comedy ever made. think about it: a severely underemployed and apathetic guy, spending all of his free time with his equally underemployed and apathetic friends talking about music and reflecting on all of the women he’d been with in the past. this sentence describes me at least seven of my closest friends, and is why this movie is a required view for any guy between 21-35.

anyway though…you’ve read my list. even though my ranking is completely undebatable, i’m curious…how does it stack up with yours?

—the champ

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Damon Young

Damon Young is the editor-in-chief of VSB. He is also a contributing editor for He resides in Pittsburgh, and he really likes pancakes.

  • Ree

    I’m always so-so with romantic comedies, most are just .. bad.

    I’ll have to check out High Fidelity. And I saw Chasing Amy once, but I fell asleep. So that one too.

    Boomerang’s a classic.

    The only romantic comedy I ever really liked enough to make it to my favorite movies of all times list is Annie Hall. That little socially inept Jewish man is hilarious.

    .. And I liked Brown Sugar, and The Best Man. ;|

    • The Champ

      woody allen’s like butter pecan ice cream…not everyones favorite, but those that like him, LOVE him.

      *this analogy made much more sense in my head*

  • Dorian G.

    What?!? No Tyler Perry???

    • The Champ

      maybe next time, when I extend my list to the top 2374, he might have a place.

      • The Killa

        HA! Couldn’t agree more!

        • Sister Toldja

          I can definitely name 2374 movies that are better than Tyler Perry’s. We have Pluto Nash comung in at 1879.

      • Dorian G.

        Well I for one am waiting for that extended list. The genius that was Diary of a Mad Black woman needs to be documented. It was romantic AND comedic. It broke new ground really.

        • The Champ


          i’m asking not to be an ass, but i’m serious curious. in your opinion, how did it break new ground?

        • The Champ

          “seriously” curious, i meant

          • Dorian G.

            LOL its sarcasm Champ. I thought it was universally accepted that the movie…left a lot to be desired.

  • Amaretto

    Hmmmm. I haven’t seen your number 1 or 3, but High Fidelity sounds interesting. I’m a Meg Ryan fan. “You’ve Got Mail”, “When Harry meet Sally” and my all time fav “French Kiss” with Kevin Kline. My heart sprouts wings and flies everytime I get to the I get to scene when Luke tells Kate that all he wants is her *sigh**looking longfullying towards the heavens*

    And what’s wrong with the Best Man? You cain’t beat a forehead kiss with a belt or a bat!

    • The Champ

      i don’t know….i can’t consider a movie to be a romantic comedy when it doesn’t have any scenes that are actually funny. the best word I can think of to describe the best man is “safe”

      • Amaretto

        I’ll see your “safe” and raise you a “not typical black movie”

        Aside from the BET shout out and the big booty stripper scene, I feel like the plot could have worked if *looks at palm* people had played the characters.

        Maybe it wasn’t funny-like a roadrunner cartoon. But I liked it because it wasn’t the single mother mad at the world, men and red kool-aid, while prayin’ to God and eatin’ big momma’s fried chicken, sucking on a watermelon rind at the cookout, while fallin’ in love with the illiterate janitor with a heart of gold.

        Wait, did I just do the treatment for the T. Perry? Darnit!

        • The Champ

          thats exactly what I mean though. if you took the same movie and replaced it with white people, it would be entirely forgettable, along the lines of drek like “the wedding planner”. I think we (black people) have been praying at the alter of “lowered movie expectations” so long that decent and safe movies such as “the best man” get branded as instant classics.

          • Deviant

            lowered expectaaaaations (c)MadTV

            • Amaretto

              LOL! I love it!

          • Amaretto

            I see your point. I HATE THE BEST MAN! It was mediocre at best. And you are right, I would have hated it if was done by palm people. Just like I hated the “Wedding Planner” there was nothing funny about that movie, not even the clothes. A movie about the 80s where the clothes and the hair didn’t even make me want to laugh. A.Damn.Shame!

            Now I LMAO at “Weekend at Bernie’s” there was no romance, but that’s a great movie I just have to say, totally randomly and slightly off topic…

            • Amaretto

              My bizzle! I was talking about the Wedding Singer, not the Wedding Planner! You see one romantic comedy you’ve seen them all. I love J.Lo’s dress when she gets married at the courthouse!

              Okay. I’m going to pretend to do some work at my job now. I’m too dazed and confused to comment anymore.

            • Deviant

              “palm people”

    • Shelia

      Amaretto, I just saw “You’ve Got Mail” and “When Harry meet Sally” for the umpteenth time last weekend. Both are great movies. Meg Ryan used to be in some great romantic comedies. I haven’t seen her in anything lately though.

      • panama

        Yeah, despite having no body of which to speak, Meg Ryan was strangely hot. I’d hit.

      • Deviant

        Meg Ryan is the Romantic Comedy Queen…

        I almost forgot about the one with her and Matthew Broderick.. Addicted to Love

  • panama

    Ya know, I’ve only seen Boomerang on this list. I’ve heard about the other two but for some reason, and despite my unhealthy fascination with romantic comedies and teen-high school-style movies (i own ‘sweet home alabama’ and ‘can’t hardly wait’ is one of my favorite movies like ever), i’m very picky when it comes to my romantic comedies.

    however, my favorite of all time is ‘love, actually’. i love that damn movie. like a lot. ‘boomerang’ is definitely up there on the list as well.

    i’d add ‘forrest gump’ except its not really romantic. basically i just wanted to share that i love forrest gump.


    • The Killa

      Everytime I see Forrest Gump someone is chopping onions or cutting grass or something because my eyes get really dusty and such….same thing with My Girl and the Lion King…I don’t know what that’s about!

      • The Champ

        I’m still mad they gave jenny aids

    • Deviant

      “Love, Actually” is a great pick.

      I watch it whenever it’s on.

    • ladyb

      Love actually is a FANTASTIC movie – and it’s hilarious – it’s actually a romance themed comedy… and i like it. a lot.

      • Vitamin Be

        I LOVED Love Actually, but for some reason i like Hugh Grant movie…Notting Hill, anyone?

  • Wise Diva

    I love all the films on your list.

    I am a ro-com fanatic, this is tough, to put in a top list, yikes.
    Eternal Sunshine Of The Spotless Mind – sci-fi AND romantic comedy, couldn’t go wrong.

    Must Love Dogs – cheesy premise, but I am just a huge Cusack enthusiast and him and Diane had cool chemistry. Their first date scene was good stuff and eerily familiar

    Love, Sex, and Eating the Bones.I heart Hill Harper to pieces. It was low budget and the cinematography kind of sucked but I love the actors in the film, and enjoyed the dialogue.

    Kissing Jessica Stein was a funny, cute, indie film.

    I was digging the Bridget Jones’ series, even though Renee’s face is kind of creepy to me.

    I think my #1 will have to be a tie between Say Anything and High Fidelity – see Cusack enthusiast!

    • Deviant

      How can you mention John Cusack and not Gross Pointe Blank???

      • Wise Diva

        eh, Minnie Driver irks me, I don’t think I ever finished it, I may have to netflix that and try again though – maybe play a drinking game this time around

        • Deviant

          Yeah she doesn’t do it for me either but it John Cusack with the added bonus of Jeremy Piven…

          That’s a winner!

          • jess

            squints… they were in a movie together?

    • The Champ

      you know, I still haven’t seen “say anything”. a friend has been begging me to watch that movie for the past 4 years, but I still haven’t gotten around to see it.

      • Deviant

        *shakes head in disgust*

        That’s like saying you haven’t seen Ferris Bueller’s Day Off…

        Please tell me you’ve seen One Crazy Summer, right?

    • Tzerai

      Still agree with you on Eternal Sunshine of the Spotless Mind (who hasn’t wanted to erase memories of an ex) and Love, Sex and Eating the Bones was very witty and intelligent.

  • Monk

    Where’s Ben Stiller or Adam Sandler????

    • The Champ

      you know, I was thisclose to putting “50 first dates” on the list, but then I realized that the stiller/sandler flicks are more “comedies that happen to have a romantic theme”.

      to make the list, the movie has to have had some serious moments and somewhat adult content, as well as the funny.

  • The Killa

    Wow man….movies errrr…yeah, that’s where the differences come out in otherwise congruent people….so MY list consists of…

    1) Jerry Maguire (cuz it damn sho ain’t a sports movie)

    2) Fifty First Dates (yes I realize I just lost 40 man points….I will still drink you under the table and fondle your woman’s breasts!)

    3) Punch Drunk Love (yes two Adam Sandler movies)

    4) Annie Hall (because I’d never want to be in a club that would have me as a member)

    and the DEFINITIVE Romantic Comedy…the one I KEEP mentioning

    5) When Harry Met Sally…..

    • The Champ

      if i extended the list to 10, jerry maquire would have definitely made the cut

  • Sister Toldja

    I agree with Boomerang, but I have to put Love Jones on my list. Even though I hate spoken word and Bill Bellamy, great flick. Larenz Tate was so fine in that movie, I was willing to date short men from 1997-1999, so long as they were Larenz Tate. Unforunately, I was 13-15 at the time, so it didn’t work out.

    I actually think Love And Basketball was a good movie as well. Good story, good character development. I think there is some film I liked better, but I am drawing a blank. Spanglish would be on my list if they didn’t fuck it to hell with the ending (the reconciliation with the crazy wife=boo). Kissing Jessica Stein was good too.

    • The Champ

      see, i consider “love and basketball” and “love jones” more “drama” than “romantic comedy”. I cant think of a single funny moment in either of those flicks

      • Sister Toldja

        That is true…..damn, we really DON’T have any Black RoCo’s, do we? I suppose it goes in hand with the lack of Black romance?

    • Shelia

      Sister Toldja, the only reason why I didn’t put love jones on my list is because I don’t really see it as a romantic comedy. I see it as a romantic movie period with drama. Love Jones is in my top 5 romantic movies of all time.

  • Monk

    What about “Shrek”?? I know I’m not the only one who loved that joint…

    • Deviant

      That’ll do, Donkey. That’ll do…

  • Single Black Male

    The best Kevin Smith movie ever … really …

    • the Killa

      ….Clerks 2….

      There, I finished that for you….