The year is 2000 and Brad Garoon and Jake Ziegler have swapped movie recommendations, resulting in wildly varying degrees of satisfaction.

Jake asked Brad to watch Wonder Boys, Curtis Hanson's charming film about Michael Douglas getting a third (or perhaps fourth or fifth) chance at love (with Frances McDormand) if he can only get over his bad habits and help his misfit friends and students. Said circle of friends is played by Robert Downey Jr., Tobey Maguire, and Katie Holmes. They talk about the terrific cameos present, Douglas's rare turn as a nicer guy, and where this ranks in Downey and Maguire's filmographies.

Brad then assigns Jake Bring It On, and Jake isn't happy about it. They discuss how Peyton Reed's movie fails when compared to other high school snapshots of the era, and how Gabrielle Union and Kirsten Dunst don't "bring" the level of quality we've come to expect of them. Can you guess which scene Brad thinks belongs in Tommy Wiseau's the Room?

Other movies discussed in this episode: The Last Detail (1973), Wall Street (1987), Clueless (1995), Election (1999), GAEA Girls (2000), Princes and Princesses (2000), Almost Famous (2000), Keeping the Faith (2000), Shadow of the Vampire (2000), High Fidelity (2000), The Contender (2000), Memento (2000), O Brother, Where Art Thou? (2000), Best in Show (2000), Crouching Tiger, Hidden Dragon (2000), You Can Count on Me (2000), Requiem for a Dream (2000), Castaway (2000), The Emperor's New Groove (2000), Traffic (2000), Diary of a Teenage Girl (2015), The Edge of Seventeen (2016), Eighth Grade (2018), Are You There God? It's Me, Margaret (2023), Bottoms (2023).