Home/Episodes/There's Something About Mary
‘There’s Something About Mary’ With Bill Simmons, Chris Ryan, and Sean Fennessey
May 5, 2026 · There's Something About Mary (1998) · Comedy · Romance · 1:49:08 · ▶ Listen on Spotify
Bill's Mount Rushmore of hardest I've ever laughed in a movie theater
Mount Rushmore · Bill Simmons · ▶ 2:32
- ·The Naked Gun (2025)▶ 2:32
- ·There's Something About Mary (1998)▶ 2:34
- ·The Hangover (2009)▶ 2:36
- ·The Silence of the Lambs (1991)▶ 2:38
Categories
Dion Waiters Award
Bill Simmons▶ 5:27Doesn't name a single specific actor; says the movie (There's Something About Mary) has essentially 10 Dion Waiters-type performances that all 'come in hot,' with Cameron Diaz singled out as becoming an A-plus lister after this movie.
Bill Simmons▶ 1:19:51Keith David ('I think it's Keith David') after initially floating Richard Jenkins and noting Harland Williams 'is pretty good'; he'd confused Keith David with Avery Brooks when reading the nominees.
Chris Ryan▶ 1:19:14Rejected the Jenkins pick ('I don't') and surfaced Keith David as the omitted nominee ('Did you say Keith David?'); predicted a contingent of listeners would go Harland Williams.
Sean Fennessey▶ 1:19:43Only clearly attributed line is a Harland Williams impression ('that old children's tale from the sea'); the 'Who'd you pick? / Keith David' exchange likely includes his answer but those lines are collapsed under Bill's attribution.
Bill's funniest movies of the 1990s
Ranked list · Bill Simmons · ▶ 10:14
- 8Dirty Work (1998)▶ 10:14
- 7Groundhog Day (1993)▶ 10:19
- 6Happy Gilmore (1996)▶ 10:21
- 5Wayne's World (1992)▶ 10:23
- 4Austin Powers: The Spy Who Shagged Me (1999)▶ 10:23
- ·Dumb and Dumber (1994)▶ 10:30
- ·Tommy Boy (1995)▶ 10:33
- ·There's Something About Mary (1998)▶ 10:34
Funniest movie by decade
Tiered list · Bill Simmons, Chris Ryan, Sean Fennessey · ▶ 10:59
1930s
- ·Bringing Up Baby (1938) · Sean Fennessey▶ 10:59
1970s
- ·Young Frankenstein (1974) · Chris Ryan▶ 11:25
- ·Animal House · Bill Simmons▶ 11:27
1990s
- ·There's Something About Mary (1998) · Bill Simmons▶ 11:49
2000s
- ·Anchorman · Sean Fennessey▶ 11:53
2010s
- ·Bridesmaids (2011) · Bill Simmons▶ 12:20
Categories, continued
Most Rewatchable Scene
Bill Simmons▶ 39:27The prom pickup scene (Ted arrives to take Mary to prom, Keith David/Markie Post, Warren attacking Ted, the 'franks and beans'/zipper gag, cops and firemen showing up) - calls it 'an unbelievable seven minutes' and 'an A plus comedy' with no notes
Chris Ryan▶ 41:32Names the Richard Jenkins therapy scene ('rest areas are the bathhouses of the 90s') as a dark-horse most rewatchable scene, while also enjoying the prom pickup sequence
Sean Fennessey▶ 39:46Agrees the prom pickup scene is flawless (especially Keith David's reactions), but doesn't single out one definitive scene of his own; also highlights the Richard Jenkins therapy scene bit as very funny
What's Aged the Best
Bill Simmons▶ 53:34The 'meat on a stick'/corn dog gag and the running use of 70s-style sitcom tropes; also specifically praises the sight gags like the hidden cum joint on Ted's ear and the Pat Healy 'Estadio Olimpico' bit as having aged well comedically
Chris Ryan▶ 53:45The 'she lives with her sister'/'chick in the armor' bit and the sweet teenage-love-story opening with young Ted and Cameron Diaz have aged well; also praises Chris Elliott's performance as still hysterical
Butch's Girlfriend Award
Bill Simmons▶ 1:05:05Tucker's plan (Lee Evans' character) - having someone break his back with a bat so Mary can treat him as an orthopedic surgeon while pretending to be an injured Englishman with a cane, all while secretly delivering pizza; Bill finds the entire scheme illogical and poorly thought out.
Chris Ryan▶ 1:04:14Jeffrey Tambor's character Sully in the theatrical cut, whose subplot is confusing because his full storyline (falling off the wagon, being eaten by a python) was cut, leaving his presence in the film unexplained.
Horlbeck Runtime Scale
Bill Simmons▶ 1:08:04119-minute runtime, so plus-19; thinks you could shave 5-10 minutes to make it tighter, but defends keeping the Hitchhiker scene and Jonathan Richmond musical segments
Chris Ryan▶ 1:08:16Would cut Jonathan Richmond and the Hitchhiker scene, joking it would get the movie down to 'like an hour,' but then walks it back saying the Hitchhiker scene is non-negotiable
Sean Fennessey▶ 1:08:57Doesn't propose cuts; says he loves the Jonathan Richmond stuff and thinks it's a great choice that feels very 90s
Stephen A. Smith Hottest Take Award
Bill Simmons▶ 1:14:24Drew Bledsoe turning down the Brett Favre role in There's Something About Mary (after the mosh pit incident) is the most underrated great thing to happen to Patriots fans, because if he'd taken it and gotten more confident/famous, Tom Brady might never have become the starter.
Chris Ryan▶ 1:11:43Ted (from There's Something About Mary) is the most deranged of the movie's male leads, more so than Tucker or Pat, due to the extreme lengths of his obsession (stalking, hiring a PI, pursuing her down I-95, getting arrested for murder).
Sean Fennessey▶ 1:13:02Ben Stiller is the greatest 'cuck'/bitch-boy actor of all time, with no real competition, given how many hit comedies are built on him being humiliated before winning the girl.
Casting What-Ifs
Bill Simmons▶ 1:16:18Lists alternate casting facts: Owen Wilson/Jon Stewart considered for Ted; Bill Murray, Vince Vaughn, Cuba Gooding Jr. considered for Pat Healy (thinks Vince Vaughn could have done it); Steve Young turned down the Brett Favre role due to film's crude content; Chris Farley reportedly turned down the role of Warren before dying during production, calls it 'probably a good miss by all parties' since it would've been distracting.
Chris Ryan▶ 1:16:31Agrees Vince Vaughn as Ted might have been 'mugging to the camera'; agrees Vaughn could work as Pat Healy; discusses Steve Young's decision to turn down the Favre role due to Mormon backlash concerns; agrees Chris Farley as Warren would have aged the movie worse and been distracting.
Sean Fennessey▶ 1:16:37Questions if Vince Vaughn was too tall for Ted, agrees he could have played Pat Healy instead.
Half-Assed Internet Research
Bill Simmons▶ 1:23:16Runs through a list of trivia facts: the scrotum-in-zipper scene was inspired by a real Farrelly Brothers family incident; Ted falling off the stretcher was an unscripted mistake (Ben Stiller actually fell and you can see him grab his arm) that they kept in the film; the waterfront Mary house in Miami was destroyed in a 2008 construction accident; the high school scene was shot at Plantation City Hall in Florida, and after seeing a raunchy rough cut the city requested no acknowledgment in the credits; also notes the hair-gel scene and that Cameron Diaz worried it would gross people out, so they shot two versions.
Chris Ryan▶ 1:24:08Notes one of the extended cut/deleted scenes involves Ted's family and backstory about his brother donating a kidney to him.
Apex Mountain
Bill Simmons▶ 1:24:33For Cameron Diaz: yes, this (There's Something About Mary) is her Apex Mountain, taking Julia Roberts' rom-com title. For Ben Stiller: 'No, not there yet.' For Matt Dillon: thinks it's in the 80s (Outsiders/Rumble Fish era). For Farrelly Brothers: agrees it's this movie, contrasting Bobby's peak vs Peter's Green Book Oscar win. Also picks Miami Vice as Apex for 'Miami movies' discussion, and Tom Hanks over Cruz for a hypothetical Mary casting.
Chris Ryan▶ 1:26:13Agrees There's Something About Mary is the Farrellys' Apex Mountain, arguing it would still sell out a screening today unlike Green Book's legacy. Also agrees Miami Vice is Apex for the Miami movies discussion, and prefers Scorsese/Cape Fear discussion over Spielberg in that comparison.
Sean Fennessey▶ 1:25:57Agrees Farrelly Brothers' Apex Mountain is There's Something About Mary, noting Peter Farrelly's later Best Picture win for Green Book doesn't top it. Also notes Cameron Diaz was more of a sex-comedy actress than rom-com actress.
Is This Movie Better With
Bill Simmons▶ 1:35:51Questions whether Robert Evans and Fergie the Florist fit, riffs on Robert Evans narrating Mary's description, doesn't land on a definitive pick
Chris Ryan▶ 1:35:15Sees potential for Fergie the Florist due to New England connection, imagines Fergie playing Ted, but ultimately isn't sold on Fergie replacing Wahlberg's role
Probably Unanswerable Questions
Bill Simmons▶ 1:37:53Rest areas as 90s hookup spots were replaced by online dating/swipe apps like Tinder; also says Ted and Mary would only date about six weeks before breaking up because he can't 'carry' the relationship with her; biggest question is how the movie never got a sequel, calling it 'the all-time layup'
Chris Ryan▶ 1:38:05Thinks Ted gets 'nuked' quickly by the Sarah Silverman and Candy Alexander characters ('doesn't last five seconds with them'); also argues the lack of a sequel is smart restraint since a bad sequel would ruin the original's integrity, and notes the premise only works pre-2008 before social media made stalking an ex plausible/trackable
Sean Fennessey▶ 1:39:10Pushes back that Farrelly Brothers weren't above sequels/remakes (cites Dumb and Dumber To, Three Stooges, Heartbreak Kid remake), so their avoidance of a sequel here is notable; also floats that Cameron Diaz being only 53 means a revival is still plausible
Who Won the Movie
Chris Ryan▶ 1:41:54Distinguishes between categories: in the moment (1998) it's Cameron Diaz, rewatching today it's Matt Dillon (surprisingly funny), but if measuring who benefited most career-wise, it's Ben Stiller
Sean Fennessey▶ 1:42:20Cameron Diaz - she's on the poster, the movie is named after her character, and it catapulted her career, even though Matt Dillon is funniest and Stiller had more long-term success
Movies Referenced (90)
Dumb and Dumber (1994)
6 mentions · Sean Fennessey, Bill Simmons, Chris Ryan▶ 10:31IMDb ↗Lb ↗
Directors Referenced (5)
Peter Farrelly
4 mentions · Sean Fennessey, Bill Simmons · Known for Green Book, There's Something About Mary, Dumb and Dumber▶ 50:22IMDb ↗Lb ↗
James Steller
3 mentions · Bill Simmons · Known for Avengers: Infinity War, The Unbearable Weight of Massive Talent, Patriots Day▶ 7:23IMDb ↗Lb ↗
Bobby Farrelly
2 mentions · Bill Simmons · Known for There's Something About Mary▶ 1:26:08IMDb ↗Lb ↗
Wes Anderson
1 mentions · Sean Fennessey · Known for Fantastic Mr. Fox, The Royal Tenenbaums, Isle of Dogs▶ 26:26IMDb ↗Lb ↗
Actors Referenced (111)
Cameron Diaz
24 mentions · Bill Simmons, Sean Fennessey, Chris Ryan · Known for Charlie's Angels, Vanilla Sky, There's Something About Mary▶ 5:46IMDb ↗Lb ↗
Brett Favre
20 mentions · Bill Simmons, Chris Ryan · Known for There's Something About Mary▶ 48:11IMDb ↗Lb ↗
Matt Dillon
20 mentions · Bill Simmons, Chris Ryan, Sean Fennessey · Known for There's Something About Mary, Crash, Drugstore Cowboy▶ 4:54IMDb ↗Lb ↗
Ben Stiller
16 mentions · Bill Simmons, Chris Ryan, Sean Fennessey · Known for Tropic Thunder, Zoolander, Zoolander 2▶ 5:53IMDb ↗Lb ↗
Keith David
13 mentions · Bill Simmons, Chris Ryan, Sean Fennessey · Known for The Princess and the Frog, They Live, Armageddon▶ 37:34IMDb ↗Lb ↗
Chris Elliott
11 mentions · Chris Ryan, Bill Simmons · Known for Groundhog Day, There's Something About Mary, The Abyss▶ 44:49IMDb ↗Lb ↗
Richard Tyson
10 mentions · Bill Simmons, Chris Ryan, Sean Fennessey · Known for Kindergarten Cop, Three O'Clock High, Black Hawk Down▶ 1:09:12IMDb ↗Lb ↗
Jonathan Richman
9 mentions · Bill Simmons, Chris Ryan, Sean Fennessey · Known for There's Something About Mary, Baby Driver, Enemy▶ 50:07IMDb ↗Lb ↗
Robert Evans
8 mentions · Bill Simmons, Chris Ryan · Known for Chinatown, Marathon Man▶ 1:35:09IMDb ↗Lb ↗
Bill Murray
7 mentions · Bill Simmons, Sean Fennessey, Chris Ryan · Known for Lost in Translation, Rushmore, Moonrise Kingdom▶ 2:38IMDb ↗Lb ↗
Norm MacDonald
7 mentions · Bill Simmons, Sean Fennessey · Known for Dirty Work, Billy Madison▶ 57:23IMDb ↗Lb ↗
Writers Referenced (6)
William Goldman
3 mentions · Bill Simmons, Chris Ryan · Known for Butch Cassidy and the Sundance Kid, All the President's Men, The Princess Bride▶ 5:04IMDb ↗Lb ↗
John J. Strauss
1 mentions · Bill Simmons · Known for There's Something About Mary, The Wild▶ 32:51IMDb ↗Lb ↗