HBO and The Ringer’s Bill Simmons is joined by Chris Ryan and Juliet Litman to induct ‘Jerry Maguire’ into the Sports Movie Hall of Fame. They discuss Rod Tidwell spin-offs, Tom Cruise Oscar snubs, the opening montage, Jonathan Lipnicki’s pinnacle, “show me the money”, the best Cruise movies, the birth of the modern sports movie, and Cruise’s romantic-lead chops.

The Ringer’s Juliet Litman and Amanda Dobbins deep dive into the 1998 romantic comedy ‘You’ve Got Mail,’ starring Tom Hanks and Meg Ryan. They discuss Tom Hank’s epic acting run in the '90s, the hallmarks of a Nora Ephron movie, the formula for a successful romantic comedy, how this movie predicts the future and hints at modern catfishing, and more.

The Ringer’s Juliet Litman, Amanda Dobbins, and K. Austin Collins sing Celine Dion and let the disaster jokes fly as they go deep on 1997’s Oscar Award–winning blockbuster ‘Titanic’ starring Leonardo DiCaprio and Kate Winslet. They discuss DiCaprio’s "cute factor," James Cameron’s obsession with the actual Titanic, and whether Rose would have chosen Jack if the ship hadn’t sunk. Learn more about your ad choices.

The Ringer's Juliet Litman, Amanda Dobbins, and K. Austin Collins pick out their trendiest '90s outfits and head to Beverly Hills to revisit the 1995 teen classic ‘Clueless,’ starring Alicia Silverstone and Paul Rudd.