The Top 20 Comedies of My Generation
In light of my recent post regarding the lack of quality movies lately, I began to contemplate what movies I would consider to be the absolute can’t miss comedies of my generation – movies released since 1990. Although there are obviously classics from every decade, to include them all into what I consider to be the time of my youth would defeat the purpose. Tastes evolve with every generation. What’s wildly amusing to one group is often lost on older people. A perfect example of this is that my father, 21 years older than I am, walked out of the movie, “Anchorman”, which I consider to be one of the finest comedies in a decade. He fails to see the humor in “He Punted Baxter!!”
The fact is, I pity the incoming generation. The movies and music that are prevalent today are excessively mediocre at best. This, in a world with an exponentially larger and more diverse landscape of choices available than ever before. It’s simply a microcosm of what passes for acceptable, and also in many cases magnifies the ordinary to extraordinary.
There is really only one criteria for whether a flick makes this list or not: Rewatchability. Different things are funny to different people – so to say one movie is better than another falls solely on taste. So in essence, the only real attribute that matters is whether you can watch the film over and over and still get close to the same enjoyment every time. There’s nothing like watching a movie for the first time – but most are only worth watching once. A motion picture that retains it’s magic through time is truly an amazing piece of art.
Ranked in order – (Rewatchability ranked on a scale on 1 (low) to 5 (high))
The Top 4
Happy Gilmore – 5 – Captures and parodies the pretentiousness of championship golf perfectly
Anchorman – 5 – Ron Burgundy is one of the greatest characters in comedic cinema.
The Big Lebowski – 5 – This is one of the very rare movies that gets better the more times you watch it.
Borat – 5 – This is probably the most rewatchable comedy ever.
The Rest
Man on the Moon – 4
Dogma – 4
Office Space – 4
Tommy Boy – 4
Me, Myself and Irene – 4
Grumpy Old Men – 3
What About Bob? – 3
Ace Ventura: Pet Detective – 3
Jay and Silent Bob Strike Back – 3
Billy Madison – 3
Dumb and Dumber – 3
Old School – 3
Wedding Crashers – 2
There’s Something About Mary – 2
American Pie – 2
The 40 Year Old Virgin – 2
See any glaring omissions to this list? Leave a comment and let me know what an idiot I am!!





Reader Comments
Love your choices – but I would probably add Best In Show and This Is Spinal Tap. We have a Monday Movie Meme you should come by and check out. And we look forward to your sports blog launch – keep us informed.
Thanks. I will definitely check your movie critiques.
I never saw Best In Show… it looks cute – I will add it to my Netflix Queue.
BTW “This Is Spinal Tap” was made in 1984.