Mrs. Parker and the Vicious Circle with Chris Feil (Chasing Gwyneth Paltrow: Episode 5)

Gwyneth Paltrow went brunette to play grieving widow Abby Janello in the 2000 romantic drama Bounce, starring alongside her recent ex Ben Affleck. We're joined by Not Aspirational host Hannah Aaron Brown to talk about Gwyneth's dogged commitment to playing a normal person, and why this movie represents the last gasp of pre-9/11 cinema. Plus: embracing your inner hoi polloi, making friends on benzos, and Toy Story fever.

Gwyneth Paltrow was supposed to star alongside Brad Pitt in the 2000 musical dramedy Duets, but after they broke up, she was forced to go it alone as Liv Dean, a woman who reunites—and then duets—with her estranged father. We're joined by Blank Check co-host Griffin Newman to talk about Gwyneth giving the worst performance of her career, and how Bruce Paltrow's illness may have made a bad movie even worse. Plus: Robert Altman Mad Libs, Aaron Sorkin's spray tan, and defending The Suicide Squad's Oscar.

Gwyneth Paltrow's first film after winning the Oscar was the 1999 thriller The Talented Mr. Ripley, where she plays Marge Sherwood, who grows increasingly suspicious of Matt Damon's titular con artist. We're joined by Screen Drafts co-host Clay Keller to talk about Gwyneth's miserable six months in Italy, and why this may just be the best movie in her filmography. Plus: spoiling Argylle, MTV Movie Awards category fraud, and how to pronounce Cate Blanchett.

Gwyneth Paltrow completed her 1998 five-film run with the period romantic dramedy Shakespeare in Love. She plays aspiring actress and Shakespeare muse Viola de Lesseps, a role which earned her her first (and, to date, only) Academy Award for Best Actress. We're joined by Be Kind Rewind host Izzy Custodio to talk about Gwyneth's most celebrated cinematic achievement, and the way this movie's aggressive Oscar campaign and Best Picture win may have unfairly tarnished it. Plus: Grace Kelly's Iron Man, Hamnet psychosis, and Billy Crystal making movie stars.

Gwyneth Paltrow's fourth 1998 movie was the thriller A Perfect Murder, a remake of Alfred Hitchcock's Dial M for Murder. She plays Emily, a U.N. translator who survives her husband's attempt to kill her and then works to uncover his plot. We're joined by writer and Who? Weekly co-host Bobby Finger to talk about Gwyneth taking on a more active role than Grace Kelly's, and how this movie may mark the moment Michael Douglas stopped being charming. Plus: accidental fetish content, the Operation Dumbo Drop soundtrack, and Roger Ebert's bugaboos.