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?

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Theme/End Music: "Diamonds" by Iouri Sazonov

Additional Music: "Storming Cinema Ident" by Edward Blakeley

Artwork: Brian O'Meara