The title; Julia Roberts' and Cameron Diaz's looks; Chicago as a character; the White Sox setting; Cameron Diaz's BMW convertible; Julia sharing the screen with Diaz; the ending; Julia's crop tops and two pairs of sunglasses; someone telling you not to smoke; the backup pact
The title has aged best: rom-coms from about 1988 to 1998 had fantastic four-word titles that explained the movie, like When Harry Met Sally, Sleepless in Seattle and While You Were Sleeping.
Julia Roberts and Cameron Diaz have aged fantastically; Julia has never looked better in a movie and Cameron Diaz probably hasn't either, both at the peak of their powers, though one host found Diaz's hairstyle too frumpy and the shift dresses too many.
Chicago is used nicely as a character: a great summer city that is minus nine with a wind chill in December, telegenic with big buildings and cool suburban spaces; it is also a White Sox movie rather than a Cubs movie, which was ahead of its time in picking the cool team, perhaps because the Cubs would not allow it or for money.
Cameron Diaz's BMW convertible, seen when she picks Julia up at the airport, is an iconic mid-90s car; the driving scenes are funny, she is a terrible driver, and it is the only point where the movie puts you in Julia Roberts' perspective.
Julia being okay battling for screen time with Cameron Diaz has aged really nicely, since most top-tier list actresses would not have been cool with that; the ending where she does not end up with him also holds up.
How beautiful Julia Roberts looks, in a style that is current again, is one host's hands-down choice: the half shirt or crop top, the two pairs of sunglasses, outfits ZoeSimmons tries to wear now, and the small sunglasses Kanye told Kim are in; smoking is not in, but having someone tell you not to smoke still is.
The concept of the backup pact, if we're not married by a certain age, really started with this movie and is now seen everywhere, having taken on a life of its own. — Amanda Dobbins
The pact's age limit of 28 is far too low and seems very early now; if someone did this today it would be more like 38, a point that had been planned for what's aged the worst.
The host running the category leaves the choice to the other two and lists candidates: the karaoke scene, Rupert Everett singing 'Say a Little Prayer' (a spouse's favorite four minutes of the movie), the 'choose me, marry me' speech, which is both crazy and heartfelt and which the hosts connect to Grey's Anatomy, Notting Hill and 90210's Kelly Taylor 'I choose me', the bathroom fight at Comiskey Park, and the ending with giant cell phones that somehow had service everywhere in 1997.
One more nominee is the boat scene, where she and Dermot Mulroney almost talk about their feelings, then dance while he sings 'The Way You Look Tonight'.
The karaoke scene is the pick because it shows the whole range of emotions for everyone involved, and Cam really brings it. — Juliet Litman
The 'Say a Little Prayer' lunch is the pick: iconic, a laugh every single time, especially the cutaway to the lobster restaurant where people in lobster mitts wave their hands; it also highlights how 90s rom-coms outside Nora Ephron's used a chirping ensemble like a musical. — Amanda Dobbins
Another host's personal favorite is the bathroom fight: the best acting of Cameron Diaz, thirty women in the women's bathroom rolling with the punches and getting mad at Julia Roberts, two famous actresses at the peak of their powers in a showdown; its climax, the 'and a food critic' jab, is parked for what's aged the worst.
The recap splits the two deciders between the karaoke scene and the lunch singing scene, both singing scenes; the helium kids appear at the Sunday brunch before the wedding and are high comedy.
