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.
Eddie Murphy Double Feature (Showtime and I, Spy)
Showtime (2002) · Sep 10, 2026
Eddie Murphy Double Feature (Showtime and I, Spy)
I Spy (2002) · Sep 10, 2026
Jackass: The Movie
Jackass: The Movie (2002) · Sep 3, 2026
The 51st State
The 51st State (2001) · Aug 27, 2026
S1m0ne (with Steve Greene)
S1m0ne (2002) · Aug 20, 2026
Eight Crazy Nights
Eight Crazy Nights (2002) · Aug 13, 2026
The Tuxedo
The Tuxedo (2002) · Aug 6, 2026
Sweet Home Alabama
Sweet Home Alabama (2002) · Jul 30, 2026
The Banger Sisters
The Banger Sisters (2002) · Jul 23, 2026
The Crocodile Hunter: Collision Course (with Taylor S. Cole)
The Crocodile Hunter: Collision Course (2002) · Jul 9, 2026
Barbershop
Barbershop (2002) · Jul 2, 2026
Brown Sugar
Brown Sugar (2002) · Jun 25, 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
Serving Sara
Serving Sara (2002) · May 21, 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
Men Dressed As Women Double Feature: Juwanna Mann and The Hot Chick
Juwanna Mann (2002) · Apr 30, 2026
Bad Company
Bad Company (2002) · Apr 23, 2026
Divine Secrets of the Ya-Ya Sisterhood
Divine Secrets of the Ya-Ya Sisterhood (2002) · Apr 16, 2026
About a Boy
About a Boy (2002) · Apr 9, 2026
The New Guy
The New Guy (2002) · Apr 2, 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
Big Trouble
Big Trouble (2002) · Mar 5, 2026
Death to Smoochy
Death to Smoochy (2002) · Feb 26, 2026
College Comedies (Sorority Boys and National Lampoon's Van Wilder)
Sorority Boys (2002) · Feb 19, 2026
College Comedies (Sorority Boys and National Lampoon's Van Wilder)
National Lampoon's Van Wilder (2002) · Feb 19, 2026
All About the Benjamins
All About the Benjamins (2002) · Feb 12, 2026
Super Troopers
Super Troopers (2001) · Jan 29, 2026
Crossroads
Crossroads (2002) · Jan 22, 2026
Birthday Girl
Birthday Girl (2001) · Jan 15, 2026
Action Spoofs: Kung Pow! Enter the Fist and Undercover Brother
Kung Pow: Enter the Fist (2002) · Jan 8, 2026
Action Spoofs: Kung Pow! Enter the Fist and Undercover Brother
Undercover Brother (2002) · Jan 8, 2026
Orange County
Orange County (2002) · Jan 1, 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
Hugh Jackman Double Feature: Someone Like You and Kate & Leopold
Kate & Leopold (2001) · Nov 20, 2025
Joe Somebody
Joe Somebody (2001) · Nov 13, 2025
Rappers in Comedies: How High and Kingdom Come
How High (2001) · Nov 6, 2025
Rappers in Comedies: How High and Kingdom Come
Kingdom Come (2012) · Nov 6, 2025
The Crime Comedies That Came Out on October 12, 2001 Double Feature (Bandits and Corky Romano)
Bandits (2001) · Oct 23, 2025
The Crime Comedies That Came Out on October 12, 2001 Double Feature (Bandits and Corky Romano)
Corky Romano (2001) · Oct 23, 2025
Serendipity
Serendipity (2001) · Oct 16, 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
Bubble Boy
Bubble Boy (2001) · Sep 18, 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
BONUS EPISODE: Roger Ebert's Wet Hot American Summer Review
Wet Hot American Summer (2001) · Aug 24, 2025
Wet Hot American Summer (with Jim Laczkowski)
Wet Hot American Summer (2001) · Aug 21, 2025
Rush Hour 2
Rush Hour 2 (2001) · Aug 14, 2025
Spoof Movies: Scary Movie 2 and Not Another Teen Movie
Scary Movie 2 (2001) · Aug 7, 2025
Legally Blonde
Legally Blonde (2001) · Jul 31, 2025
America's Sweethearts
America's Sweethearts (2001) · Jul 24, 2025
Pootie Tang
Pootie Tang (2001) · Jul 17, 2025
Martin Lawrence Double Feature (What's the Worst That Could Happen and Black Knight)
Black Knight (2001) · Jul 10, 2025
Martin Lawrence Double Feature (What's the Worst That Could Happen and Black Knight)
What's the Worst That Could Happen? (2001) · Jul 10, 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
Just Visiting
Just Visiting (2001) · May 8, 2025
Men Behaving Badly Double Feature (Tomcats and Shallow Hal)
Shallow Hal (2001) · May 1, 2025
Men Behaving Badly Double Feature (Tomcats and Shallow Hal)
Tomcats (2001) · May 1, 2025
Say It Isn't So
Say It Isn't So (2001) · Apr 24, 2025
Heartbreakers (with Mitchell Beaupre)
Heartbreakers (2001) · Apr 17, 2025
Morris Chestnut Double Feature (The Brothers and Two Can Play That Game)
The Brothers (2001) · Apr 10, 2025
Morris Chestnut Double Feature (The Brothers and Two Can Play That Game)
Two Can Play That Game (2001) · Apr 10, 2025
Get Over It (with Taylor Cole)
Get Over It (2001) · Apr 3, 2025
The Mexican
The Mexican (2001) · Mar 27, 2025
Monkeybone
Monkeybone (2001) · Mar 20, 2025
Down to Earth
Down to Earth (2001) · Mar 13, 2025
Saving Silverman
Saving Silverman (2001) · Mar 6, 2025
Freddie Prinze, Jr. Double Feature: Head Over Heels and Summer Catch
Summer Catch (2001) · Feb 27, 2025
The Wedding Planner
The Wedding Planner (2001) · Feb 20, 2025
Sugar and Spice
Sugar and Spice (1997) · Feb 13, 2025
Orlando Jones Double Feature: Double Take and Evolution
Evolution (2001) · Feb 6, 2025
Orlando Jones Double Feature: Double Take and Evolution
Double Take (2001) · Feb 6, 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
Lucky Numbers
Lucky Numbers (2000) · Dec 19, 2024
Devil Comedies: Bedazzled and Little Nicky
Little Nicky (2000) · Dec 12, 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
Nurse Betty
Nurse Betty (2000) · Nov 14, 2024
Beautiful Women and Awful Men (Whipped and Woman on Top)
Woman on Top (2000) · Nov 7, 2024
Beautiful Women and Awful Men (Whipped and Woman on Top)
Whipped (2000) · Nov 7, 2024
Bring It On (with Mitchell Beaupre)
Bring It On (2000) · Oct 24, 2024
The Replacements
The Replacements (2000) · Oct 17, 2024
Coyote Ugly
Coyote Ugly (2000) · Oct 10, 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
Shanghai Noon
Shanghai Noon (2000) · Aug 29, 2024
Small Time Crooks
Small Time Crooks (2000) · Aug 22, 2024
Road Trip
Road Trip (2000) · Aug 15, 2024
American Psycho
American Psycho (2000) · Jul 25, 2024
Return to Me
Return to Me (2000) · Jul 11, 2024
High Fidelity (With Taylor Cole)
High Fidelity (2000) · Jul 4, 2024
Whatever It Takes
Whatever It Takes (2000) · Jun 27, 2024
60s Best Director Spectacular: The Next Best Thing and What Planet Are You From?
The Next Best Thing (2000) · Jun 20, 2024
Drowning Mona
Drowning Mona (2000) · Jun 13, 2024
Wonder Boys
Wonder Boys (2000) · Jun 6, 2024
Hanging Up
Hanging Up (2000) · May 23, 2024
Down to You
Down to You (2000) · May 16, 2024
Sports Comedies: Play It to the Bone and Ready to Rumble
Play It to the Bone (1999) · May 9, 2024
Next Friday
Next Friday (2000) · May 2, 2024
Tripp's Pick: The Red Violin
The Red Violin (1998) · Apr 25, 2024
Galaxy Quest
Galaxy Quest (1999) · Apr 11, 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
The Best Man
The Best Man (1999) · Mar 7, 2024
Superstar
Superstar (1999) · Feb 28, 2024
Small Town Comedies: Mumford and Mystery, Alaska
Mystery, Alaska (1999) · Feb 22, 2024
Small Town Comedies: Mumford and Mystery, Alaska
Mumford (1999) · Feb 22, 2024
Three Kings
Three Kings (1999) · Feb 15, 2024
Buddy Action Comedy: Chill Factor and Blue Streak
Chill Factor (1999) · Feb 8, 2024
Love Stinks
Love Stinks (1999) · Feb 1, 2024
High School Romance: Outside, Providence and Drive Me Crazy
Drive Me Crazy (1999) · Jan 25, 2024
High School Romance: Outside, Providence and Drive Me Crazy
Outside Providence (1999) · Jan 25, 2024
Teaching Mrs. Tingle
Teaching Mrs. Tingle (1999) · Jan 11, 2024
Mickey Blue Eyes
Mickey Blue Eyes (1999) · Jan 4, 2024
Go (with Jim Laczkowski)
Go (1999) · Dec 28, 2023
Detroit Rock City
Detroit Rock City (1999) · Dec 21, 2023
Mystery Men
Mystery Men (1999) · Dec 14, 2023
Bowfinger
Bowfinger (1999) · Dec 7, 2023
Drop Dead Gorgeous
Drop Dead Gorgeous (1999) · Nov 23, 2023
American Pie
American Pie (1999) · Nov 9, 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
Julia Roberts: Notting Hill and Runaway Bride
Notting Hill (1999) · Oct 12, 2023
Idle Hands
Idle Hands (1999) · Oct 5, 2023
Pushing Tin
Pushing Tin (1999) · Sep 28, 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
High Concept Comedies: Blast from the Past and EdTV
Blast from the Past (1999) · Aug 24, 2023
Forces of Nature
Forces of Nature (1999) · Aug 17, 2023
Analyze This
Analyze This (1999) · Aug 10, 2023
High School Adaptations: She's All That and 10 Things I Hate About You
She's All That (1999) · Aug 3, 2023
Office Space
Office Space (1999) · Jul 26, 2023