The Ringer's Juliet Litman and Amanda Dobbins are joined by Bill Simmons to discuss Reese Witherspoon's sprawling catalog (5:00), her relationship with Ryan Phillippe (12:00), her R-rated turn in 'Cruel Intentions' (16:00), her missed opportunity with 'Clueless' (23:00), her Oscar curse (29:00), her fling with Jake Gyllenhaal (36:00), her comeback with 'Gone Girl' (43:00), and her next big career move after 'Big Little Lies' (48:00).
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