Asked whether this is the Apex Mountain of rom-coms, the first answers are a flat no, twice, before the hosts call it essential to the genre, top five for one, the first to twist the rom-com gimmick and the last place the genre could go; whether it is the apex before the genre went downhill draws only a maybe, a case could be made, and a flat not convinced.
The twist and the respect for the rom-com form are liked, since it gets the impulse to see people together before twisting it; Notting Hill in 1999 is raised as a further meta-commentary that is really Julia Roberts' life, with her playing a bad person there too.
Rupert Everett is a 100 percent yes, an iconic performance and the breakout element the movie needed alongside the comeback star and the second star; he went on to the Madonna movie, which has not aged well, had James Bond talk about whether he could be the first gay Bond, and this remains his most mainstream and most fun performance beside period pieces like Madness of King George and The Importance of Being Earnest.
Cameron Diaz is not at her apex here, though she is really good; her apex is There's Something About Mary, a massive movie that arguably deserved an Oscar nomination and made her a gigantic star, after which she dated Matt Dillon and entered the Us Weekly stream.
Her dating history is called rough by one host because it never worked out, and impressive by another: Justin Timberlake, the baseball player known as A Rod, a broken nose surfing; the JT age gap is compared to Sandra Bullock and Ryan Gosling.
Julia Roberts is a yes: Pretty Woman blew her up, but this movie re-established her as the most bankable, A plus list actress, set up the next five years and led to her Oscar, so it righted the ship; one voice finds that reasonable, and Ocean's Eleven is floated for her astonishing but not lead role.
Chicago as an Apex Mountain is rejected as insulting; Dermot Mulroney is a yes for sure, since it never got better, or worse, for him.
An early aside calls 1997 and this film arguably the apex of rom-coms, the top of the crescendo, after which the genre went off a cliff a little.
Before the categories, one host previews that Cameron Diaz's Apex Mountain is There's Something About Mary, a role nobody else could have played as likable, funny and slapstick.
The Christian storyline, though the hosts move it toward aged pretty well; Christian's over-stylized retro persona; how the teenagers interact, such as Elton keeping Cher's photo in his locker; Murray and Elton sharing a popular crew; Cher and Ty doing a home workout video; the fashion computer's monitor
Cher's date with Christian is called the most problematic part of a problematic fave; asked whether falling for a gay man is a rom-com trope, the hosts can only think of the Rupert Everett and Madonna film and agree it is not really a rom-com thing, while finding it funny that the straight guys, Paul Rudd seeing Christian dance with a man and Murray, pick up on it before the ostensibly perceptive Cher and Dion.
Murray's reveal, played as a clip, uses 'friend of Dorothy', an old-school gay self-identifying marker from The Wizard of Oz, plus 'cake boy' and the Oscar Wilde, disco-dancing, Streisand-ticket-holding string; the hosts find it hilarious in a good way that Amy Heckerling put those words in Murray's mouth, call the Streisand line remarkable and Pulitzer-worthy, and the 'cake boy' line unfortunate.
Christian's analog in Emma, read from Wikipedia in a way Cher would endorse since she loves Cliff's Notes, is Frank Churchill, who courts Emma while secretly engaged to someone else and waiting on an aunt's inheritance, so the storylines are not really the same; the host prefers him being gay to that.
GLAAD ('Glad' as transcribed) gave Amy Heckerling an award for the storyline, which was very progressive at the time; Murray pointing out that Christian is gay is not malicious, the joke is that Cher is totally clueless, which one host says has happened to teenage girls and, going by the friends that host still counsels through it, women of all ages, so the item is moved to somewhere between aged best and aged pretty well.
What still annoys is Christian's style: the over-stylized guy obsessed with the twenties and thirties, who deserves Cher not knowing who Billie Holiday is, though Billie Holiday deserves better.
Discussing a possible remake, the hosts find the way these kids interact foreign to teenagers now; Elton keeping a photo Cher took in his locker is quaint, silly and confusing, which is part of why Elton gets kicked out of the picture because he sucks, and the 'social director of the crew' line is loved.
Murray and Elton being in the same crew of popular guys confuses one host, whose high school popular set was uniform in style rather than race; another went to a weird school with a wide range, and a third had a clearly defined cool tier with pressure to look the same, so the kids with sagging jeans and the Eltons would have mutually rejected each other.
Cher and Ty doing a home workout video instead of a class has aged badly, though it is set in the nineties when everyone had workout videos; the hosts recall sneaking a mother's 'Tybo' tape (as transcribed), a Paula Abdul video with a routine still remembered, and the Barbie workout video starring Jennifer Love Hewitt.
Earlier, during the opening-minutes discussion, the fashion computer's actual monitor is said to look like trash now and not to have aged well, even though the idea was forward thinking.