This week on the season finale of And the Runner-Up Is, Kevin welcomes back writer and podcaster Morgan Roberts to discuss the 1999 Oscar race for Best Actress, where Hilary Swank won for her performance in "Boys Don't Cry," beating Annette Bening in "American Beauty," Janet McTeer in "Tumbleweeds," Julianne Moore in "The End of the Affair," and Meryl Streep in "Music of the Heart." We discuss all of these nominated performances and determine who we think was the runner-up to Swank. 0:00 - 10:09 - Introduction 10:10 - 30:37 - Annette Bening 30:38 - 50:37 - Janet McTeer 50:38 - 1:08:14 - Julianne Moore 1:08:15 - 1:26:06 - Meryl Streep 1:26:07 - 1:52:39 - Hilary Swank 1:52:40 - 2:55:42 - Why Hilary Swank won / Twitter questions 2:55:43 - 3:01:20 - Who was the runner-up? Buy And the Runner-Up Is merch at https://www.teepublic.com/stores/and-the-runner-up-is?ref_id=24261! Support And the Runner-Up Is on Patreon at patreon.com/andtherunnerupis! Follow Kevin Jacobsen on Twitter Follow Morgan Roberts on Twitter Follow And the Runner-Up Is on Twitter and Instagram Theme/End Music: "Diamonds" by Iouri Sazonov Additional Music: "Storming Cinema Ident" by Edward Blakeley Artwork: Brian O'Meara