2000 had Best in Show which I might put above Road Trip and also had Meet the Parents which should get an HM.
2001 had American Pie 2/balls, and two underrated one - Saving Silverman and Rat Race
2003 Had Bad Santa and Elf - neither as good as Old School but a pretty good Holiday season for movies.
The Best in Show crew can be hit or miss with me. I feel like I need to be in the right mood to laugh at their stuff. Like, be all sophisticated and stuff.
Saving Silverman is hysterical. The lampshade scene makes me laugh every single time.
AND Fugly JENNINGS IS FUGLY!!!!! Awful White Female Liberal: Eat a dick kite
**disclaimer - I googled "Comedy Movies <insert year>" and scrolled across the ones that showed up in the image bar at the top of the results page. If your movie wasn't there, it wasn't considered.
2000 - Road Trip, Scary Movie, Miss Congeniality, O. Brother Where Are Thou?, and Meet The Parents are strong. The winner is Best in Show.
2001 - Zoolander, Joe Dirt, Wet Hot American Summer, Shallow Hal, American Pie 2, and Super Troopers are good. Shrek is better.
2002 - Austin Powers' Goldmember....not as good as the others, but better than anything else in this weak year that includes Mr. Deeds, The New Guy, Jackass, and Van Wilder
2003 - Old School in a romp over School of Rock, Bruce Almighty, Freaky Friday, and Finding Nemo
2004 - Holy fuck, what a great year.....The Girl Next Door, DodgeBall, Napolean Dynamite, Mean Girls, Anchorman, Euro Trip, Shaun of the Dead, Kung Fu Hustle, and your winner.....Team America, World Police
2005 - Wedding Crashers squeaks by 40-Year Old Virgin and Waiting
2006 - Talladega Nights tops Borat in the finals, nice year Sacha
2007 - Superbad wins but don't sleep on Walk Hard
2008 - Another big year with Role Models, Zack and Miri Make a Porno, Semi-Pro, Step Brothers, House Bunny, and Forgetting Sarah Marshall being beat out by your winner Tropic Thunder
2009 - The Hangover wins, but don't pass on I Love You, Beth Cooper, it's a good throwback comedy. Zombieland was considered here, as well.
2010 - Easy A is good, Date Night is formulaic but has moments. I like Red and She's Out of My League and dislike the overrated Get Him to the Greek. The winner here is the vastly underappreciated The Other Guys
2011 - For smart comedy, look to Crazy, Stupid Love. Bride's Maids is strong, as well. Hall Pass, Just Go With It, Take Me Home Tonight and Tower Heist are okay. The best of the best is Horrible Bosses.
2012 - Silver Linings Playbook is really good, so is Pitch Perfect. Wanderlust and This is 40 kinda suck. 21 Jump Street comes from nowhere to win this year.
2013 - We're the Miller is alright, This is the End was funny, and I won't count The Wolf of Wall Street as a comedy. Pain and Gain contends, Anchorman 2 does not. The Heat earns the silver as the gold goes to the little-seen Jason Bateman vehicle Bad Words.
2014 - Not a great year. Lego Movie, 22 Jump Street, Let's Be Cops, Walk of Shame, and Neighbors all fall behind Ride Along.
2015 - Sisters was blah. Daddy's Home was okay. Get Hard and Mr. Right were funny, but this year's champ is Trainwreck.
2016 - Central Intelligence, Bad Moms, Popstar, Deadpool, and Good Kids are pretty good. The criminally underrated The Nice Guys is my pick.
2017 - Yikes. Horrible year. Go with Thor Ragnarok.
2018 - Blockers, Deadpool 2 and Tag lose to Game Night.
2019 - I won't call Once Upon A Time in Hollywood a comedy. Good Boys, Zombieland 2, and Jojo Rabbit contend, but Knives Out wins.
2020 - Stream something from the last 19 years instead.
Isn't it a little racist to call it Black Friday? - Joy Behar
Good list, Dong. I'll give some additional thoughts on each year, but ultimately I agree with almost all of your winners. Man did things start getting rough around 2013.
2000: You got it right, but I'd throw HMs to Me, Myself, and Irene and Scary Movie. 2001: Obviously I agree with Super Troopers, and your HMs are the correct choices too. But I love a lot of others - Joe Dirt, AP2, Jay & Silent Bob Strike Back, Pootie Tang... Man, what a year. 2002: Jackass is correct, but kudos to LDOT for mentioning the 2 others I'd have considered. 2003: I'm just gonna go ahead and say it... Bad Santa warrants mentioning. I'm not saying it's better than Old School, but I'm willing to have a discussion about it. 2004: Another murderer's row of hilarious films. Euro Trip was that year too. 2005: I guess it's not in the same class as the ones you picked, but The Ringer (dot com) is a crimininally underrated movie. 2006: Agreed. The rest of this year sucks. Like, a lot. I still haven't seen Idiocracy; I DVR'd it on HBO a few weeks ago, will prob watch soon. 2007: I'd go with Walk Hard over Superbad, but it's really close. Agreed that's a very tough call. 2008: My search indicates FSM also came out this year. It's at least an HM. Pineapple Express sucked and does not deserve to be mentioned, let alone honarably. 2009: The Hangover was great, but I'm picking Zombieland. The most egregious omission from this whole list IMO. I Love You, Man was pretty good, too. Never saw Fantastic Mr. Fox. 2010: Agree it's HTTM. I think I'm the only person who didn't love The Other Guys. I'm giving Kick Ass and Easy A HMs over that. 2011: Horrible Bosses over Bridesmaids, and it's not remotely close. Crazy Stupid Love is also better than Bridesmaids, and maybe even Hangover 2. Also, TIL there was a Mean Girls 2. 2012: I'm shocked you didn't include Pitch Perfect as an HM here. Ted seems worthy of an HM too, IMO. 2013: Brutal year. Does Wolf of Wall Street count? If not, I guess I'll go with We're the Millers. HM to Anchorman 2 and Kick Ass 2. 2014: Oof. The only other decent choices that year were Horrible Bosses 2 and The Lego Movie. 2015: I didn't see Spy, so give me Daddy's Home by a hair over Vacation. 2016: I liked Sausage Party and Bad Moms, but yeah, Pop Star sounds right. No wait... I might go with Deadpool; this is a close one. 2017: Didn't see Thor. Wow this is a terrible year... I guess I'll take Jumanji. Daddy's Home 2 is the only other one I can even consider. 2018: Yuck. I watched Tag recently. It's OK-ish, easily the 2nd funniest movie of the year. 2019: Good Boys is probably right. HM to Zombieland Double Tap and Jumanji The Next Level. I also really liked Knives Out, if that counts as a comedy. 2020: I've seen nothing from this year besides children's movies. I guess I'll go with Scoob over Sonic The Hedgehog and Dolittle.
Might as well keep it going, starting with an absolute absurd collection: 1999-South Park BLU is my pick. Here are the honorable mentions *deep breath* Austin Powers 2, Election, Life, Analyze This, Office Space, Galaxy Quest, Big Daddy, Blue Streak, Duece Bigalow, 10 Things I Hate About You and American Pie) 1998--Something About Mary--HM-Half Baked, Big Lebowski, Rush Hour, Dirty Work, The Waterboy, Can't Hardly Wait, Wedding Singer, Rushmore, Baseketball 1997--Austin Powers--HM Men in Black, Liar Liar, Vegas Vacation, Chasing Amy, Grosse Pointe Blank 1996--Happy GIlmore (HM--Swingers, Don't Be a Menace, Down Periscope, Bio-Dome, Fargo (not a strict comedy or probably my #1), Multiplicity, Kingpin, Cable Guy, Beavis & Butthead 1995--Tommy Boy (HM--Billy Madison, Clueless, Mallrats, Friday, Bad Boys, Toy Story, Ace Venture 2, Brady Bunch Movie) 1994-- Dumb & Dumber (HM--Clerks, The Mask, Ace Ventura) 1993--Groundhog Day (HM--Dazed & Confused, Robin Hood Men in Tights, Mrs Doubtfire, Grumpy Old Men, Dave) 1992--My Cousin Vinny (HM Waynes World, Encino Man, White Men Can't Jump, Class Act, Boomerang) 1991--Necessary Roughness (HM-Doc Hollywood, Soap Dish, Naked Gun 2 1/2, Hot Shots, Don't Tell Mom The Babysitter's Dead, Nothing But Trouble (because of how truly awful it is) 1990--(This is a pain in the ass b/c it tries to give you 90s movies)--Home Alone (HM--Kindergarten Cop, Men at Work, My Blue Heaven, House Party, Joe vs the Volcano)