Tripp has rejected mainstream comedies for most of his life. Now, Ross is taking him film by film through the movies he sadly missed (or smartly avoided) until now. Join us as we look at studio comedies from the late 90s and early 2000s. Week by week, we will tackle one (or two) films as Tripp tries to figure out what made them so funny and Ross explains the context Tripp avoided.
The Crocodile Hunter: Collision Course (with Taylor S. Cole)
The Crocodile Hunter: Collision Course (2002) · Jul 9, 2026
The Master of Disguise (with Ben Coller)
The Master of Disguise (2002) · Jun 11, 2026
The Adventures of Pluto Nash
The Adventures of Pluto Nash (2002) · Jun 4, 2026
Eight Legged Freaks (with Mike Merrigan and Jay Santo)
Eight Legged Freaks (2002) · May 28, 2026
Men in Black II
Men in Black II (2002) · May 14, 2026
Mr. Deeds (with Mitchell Beaupre)
Mr. Deeds (2002) · May 4, 2026
Mr. Deeds (with Mitchell Beaupre)
Mr. Deeds Goes to Town (1936) · May 4, 2026
Divine Secrets of the Ya-Ya Sisterhood
Divine Secrets of the Ya-Ya Sisterhood (2002) · Apr 16, 2026
Life or Something Like It
Life or Something Like It (2002) · Mar 26, 2026
My Big Fat Greek Wedding
My Big Fat Greek Wedding (2002) · Mar 19, 2026
The Sweetest Thing
The Sweetest Thing (2002) · Mar 12, 2026
Death to Smoochy
Death to Smoochy (2002) · Feb 26, 2026
All About the Benjamins
All About the Benjamins (2002) · Feb 12, 2026
Super Troopers
Super Troopers (2001) · Jan 29, 2026
Bonus Season: Charlie's Angels
Charlie's Angels (2000) · Dec 25, 2025
Bonus Season: Varsity Blues
Varsity Blues (1999) · Dec 11, 2025
Tripp's Pick: No Man's Land
No Man's Land (2001) · Dec 4, 2025
Zoolander (with Steve Greene)
Zoolander (2001) · Oct 9, 2025
Rock Star (with Mik Dempsey)
Rock Star (2001) · Oct 2, 2025
Jay and Silent Bob Strike Back
Jay and Silent Bob Strike Back (2001) · Sep 25, 2025
Rat Race (with Thomas Todd)
Rat Race (2001) · Sep 11, 2025
American Pie 2
American Pie 2 (2001) · Sep 4, 2025
The Princess Diaries
The Princess Diaries (2001) · Aug 28, 2025
Wet Hot American Summer (with Jim Laczkowski)
Wet Hot American Summer (2001) · Aug 21, 2025
Legally Blonde
Legally Blonde (2001) · Jul 31, 2025
America's Sweethearts
America's Sweethearts (2001) · Jul 24, 2025
One Night at McCool's
One Night at McCool's (2001) · Jul 2, 2025
The Animal (with Mike Merrigan)
The Animal (2001) · Jun 26, 2025
Freddy Got Fingered
Freddy Got Fingered (2001) · Jun 19, 2025
"Crocodile" Dundee in Los Angeles
Crocodile Dundee in Los Angeles (2001) · Jun 5, 2025
Bridget Jones's Diary
Bridget Jones's Diary (2001) · May 29, 2025
Josie and the Pussycats
Josie and the Pussycats (2001) · May 22, 2025
Joe Dirt (with Jake Ziegler)
Joe Dirt (2001) · May 15, 2025
Say It Isn't So
Say It Isn't So (2001) · Apr 24, 2025
Heartbreakers (with Mitchell Beaupre)
Heartbreakers (2001) · Apr 17, 2025
Get Over It (with Taylor Cole)
Get Over It (2001) · Apr 3, 2025
Saving Silverman
Saving Silverman (2001) · Mar 6, 2025
The Wedding Planner
The Wedding Planner (2001) · Feb 20, 2025
Sugar and Spice
Sugar and Spice (1997) · Feb 13, 2025
Tripp's Pick: The Girl on the Bridge
The Girl on the Bridge (1999) · Jan 23, 2025
Miss Congeniality
Miss Congeniality (2000) · Jan 9, 2025
What Women Want
What Women Want (2000) · Jan 2, 2025
The Ladies Man (with Aaron Neuwirth)
The Ladies Man (2000) · Dec 26, 2024
Dude, Where's My Car?
Dude, Where's My Car? (2000) · Dec 5, 2024
Meet the Parents (with Alex Perlman)
Meet the Parents (2000) · Nov 28, 2024
Dr. T and the Women
Dr. T & the Women (2000) · Nov 21, 2024
Bring It On (with Mitchell Beaupre)
Bring It On (2000) · Oct 24, 2024
The Replacements
The Replacements (2000) · Oct 17, 2024
Nutty Professor II: The Klumps
Nutty Professor II: The Klumps (2000) · Oct 3, 2024
Scary Movie (with Mike Merrigan)
Scary Movie (2000) · Sep 19, 2024
Me, Myself and Irene
Me, Myself & Irene (2000) · Sep 12, 2024
Big Momma's House
Big Momma's House (2000) · Sep 5, 2024
Small Time Crooks
Small Time Crooks (2000) · Aug 22, 2024
American Psycho
American Psycho (2000) · Jul 25, 2024
High Fidelity (With Taylor Cole)
High Fidelity (2000) · Jul 4, 2024
Whatever It Takes
Whatever It Takes (2000) · Jun 27, 2024
Tripp's Pick: The Red Violin
The Red Violin (1998) · Apr 25, 2024
Deuce Bigalow: Male Gigolo
Deuce Bigalow: Male Gigolo (1999) · Apr 4, 2024
Anywhere But Here
Anywhere but Here (1999) · Mar 28, 2024
Dogma (with Mike Merrigan)
Dogma (1999) · Mar 21, 2024
Teaching Mrs. Tingle
Teaching Mrs. Tingle (1999) · Jan 11, 2024
Mickey Blue Eyes
Mickey Blue Eyes (1999) · Jan 4, 2024
Detroit Rock City
Detroit Rock City (1999) · Dec 21, 2023
Drop Dead Gorgeous
Drop Dead Gorgeous (1999) · Nov 23, 2023
Big Daddy (with Mitchell Beaupre)
Big Daddy (1999) · Nov 2, 2023
South Park: Bigger, Longer, and Uncut
South Park: Bigger, Longer & Uncut (1999) · Oct 26, 2023
Austin Powers: The Spy Who Shagged Me
Austin Powers: The Spy Who Shagged Me (1999) · Oct 19, 2023
Lost and Found
Lost and Found (2019) · Sep 21, 2023
Never Been Kissed
Never Been Kissed (1999) · Sep 7, 2023
The Out-of-Towners
The Out-of-Towners (1970) · Aug 31, 2023
Forces of Nature
Forces of Nature (1999) · Aug 17, 2023
