Seann William Scott performance ages well; Old School animal trainer preferred by one; Goon career gamble, larger career expectations and Owen Wilson market-correction explanation disputed.
Finch stands out; Eddie K. Thomas expected Cusack-like career, character mature persona and sitcom trajectory discussed.
Coolidge room-scene comic performance remains memorable. — Bill Simmons
Film popularized rather than necessarily invented MILF term; Shampoo comparison and John Cho scene praised. — Sean Fennessey
Jim family portrait and bandcamp joke still funny despite latter becoming annoying. — Bill Simmons
Hannigan vocal resemblance to Greta Gerwig jokingly proposed; host reports wife praising Tara Reid performance. — Bill Simmons
Shannon Elizabeth explicitly nominated for aged best: late-90s Maxim and Stuff stardom, later poker success and magazine-selling ability recalled, with uncertainty about how far the fame carried her.
New wrapper 24 years-later reassessment: Jennifer Coolidge White Lotus and Eugene Levy Schitts Creek became belated breakout stars; retrospective pair distinguished from original ballot discussion. — Bill Simmons
Coolidge's part in the Bend and Snap is said to cloud her performance; Selma Blair is famous without a clear reason; giving the award to the Bend and Snap scene is floated. — Juliet Litman
The opening song sets the mood, as with Suddenly I See in The Devil Wears Prada; 2000s theme songs like the Hills' Unwritten stepped up their game. — Bill Simmons
Her sparkly, clearly non-waterproof bikinis are back as festival wear. — Juliet Litman
The garish early-2000s fashion is a cautionary tale and time capsule; the daughter found only four of 40-plus outfits wearable now, including the pink top with low-rise jeans, the polka-dot internship dress and the new-representation pink suit.
The belted green sweater at the start of law school is called her best outfit. — Juliet Litman
The snooty salesperson who gets a comeuppance is a Pretty Woman homage. — Bill Simmons
'Law school is for people who are ugly, boring and serious' is funny; the lesbians-against-drunk-driving joke pushed the envelope for 2001. — Bill Simmons
The tone has aged well because it mocks the right things without blonde shaming. — Amanda Dobbins
Jon Hamm as Ted; the gate-swing opening; Wendi McLendon-Covey as Rita; the $12 workout; Annie's store scenes; Jill Clayburgh casting; the cupcake scene and baking; Annie's mom's paintings; money and wedding absurdity; weddings as a movie trope; Helen's stepkids and lines; Wilson Phillips ending; ensemble performances; R-rated scatological humor; Milwaukee
Jon Hamm, in three scenes, escapes the Don Draper typecasting by playing the ultimate douchebag; "I really want you to leave, but I don't know how to say it without sounding like a dick" is the iconic line. — Bill Simmons
The opening gate swing of shame and Annie sneaking back into bed establish her character in two minutes. — Mina Kimes
Ted is a textbook narcissist everyone sees through, and making him horrible at sex is a great choice. — Mallory Rubin
The rich douchebag in relation to a woman reverses usual comedy roles; Hamm looks like an actor on vacation in a well-written part of nine or ten minutes, down to the Porsche.
Jennifer Coolidge was considered as an alternative for Rita but would have been distracting; McLendon-Covey is more subtle and would not be recast. — Mina Kimes
Rita's lines, including the semen blanket and her nine-year-old telling her to fuck off over pizza, remind viewers that married life is not idyllic. — Mallory Rubin
Other holdovers: stealing Terry Crews's class to save $12, Annie's bad store work, the Jill Clayburgh casting, and the Bo Cosby joke. — Bill Simmons
The Fiona Apple song over the cupcake scene is noted, with Maya Rudolph married to Fiona Apple's ex Paul Thomas Anderson; the scene shows how broken Annie is about baking.
Baking in general in the Great British Bake Off era, including the cupcake leaf and the carrot cake, holds up. — Bill Simmons
Annie's mom's celebrity paintings, including Taylor Swift, are a subtle touch; her AA character outs people, including Bo Cosby.
Money, and how dumb and expensive weddings are, have aged well; the wedding industrial complex is real.
Weddings work as a movie trope because they put all the characters in one place; weddings also drive people crazy. — Bill Simmons
One participant recounts the only fight with their dad, three weeks before their wedding, over inviting a cousin's boyfriend to a guest list capped around 100-125. — Bill Simmons
Helen's stepkids and her 11 or 12 passive-aggressive lines, including the drink-passing line on the plane, are favorites.
The ensemble performances, scatological humor and explicit R-rated comedy hold up; Milwaukee and Pittsburgh are underrated cities, and the "cock baby" graffiti is a favorite.
