Jake Gyllenhaal on Picking Roles, Filming in Boston, and Creating Characters (Ep. 265)

HBO's Bill Simmons proves you're never too old to watch 'The Challenge.' It's a good old fashioned grab bag simulcast w/ Juliet discussing Tony's libido (3:00 mark), Nany's new-found confidence (12:00), Johnny Bananas' knack for toasting (14:00), Jenna vs. Brianna (31:00) and C.T.'s inevitable return to TV (38:00). Next up, Chris Ryan comes on to chat about 'Survivor' (41:00), the Sixers' new addition (52:00), Russell Westbrook's real estate dealings (56:00) and Gordon Hayward's decked out Hacienda style home(1:02:00). Learn more about your ad choices. Visit podcastchoices.com/adchoices

10 Des 20151h 5min

HBO's Bill Simmons catches up with Katie Nolan on the Left Coast. Topics include: L.A. sports scene (3:00 mark), Larry Bird's 59th birthday (14:00), Tom Brady's end-of-career ability (20:00), current NFL model (26:00), Katie and Jaromir Jagr's uncanny haircut (37:00), social media etiquette (48:00), Jamie Horowitz's Kobe Bryant comparison (57:00) and NHL support in November (1:05:00). Learn more about your ad choices. Visit podcastchoices.com/adchoices

9 Des 20151h 11min

HBO's Bill Simmons brings on Cousin Sal to talk Week 14 NFL Picks and a possible playoff picture. Topics: Belichick's recent struggles (3:00), Pitt/Sea playoff chances (8:00), Harry Styles' GB allegiance (18:00), Jeff Fisher's mustache (25:00), Sly's Oscar speech (37:00), Sean Payton's sabbatical(46:00), NFL ROY race (57:00), Tom Coughlin's next stop(1:05:00) and the 'Rocky' franchise(1:10:00). Learn more about your ad choices. Visit podcastchoices.com/adchoices

7 Des 20151h 14min

HBO's Bill Simmons chats with Joe House about Green Bay's Hail Mary, Kobe's last stand (10:00), Kobe vs. Duncan (17:00), the floundering Wiz (22:00), Paul George (26:00), Stephen Curry's historic 20-game run (36:00), 20 crazy Curry stats (42:00), Curry vs. MJ (50:00) and best Week 13 NFL bets (1:00:00). Learn more about your ad choices. Visit podcastchoices.com/adchoices

4 Des 20151h 19min

HBO's Bill Simmons brings in his buddy JackO to discuss Boston's David Price signing, then Trump and the Republicans (23:00). Then, Michael Rapaport talks Kobe's bizarre farewell tour (38:00) and flawed NBA rebuilding plans (44:00). And finally, original Grantlander Jay Caspian Kang talks Kobe's demise & NBA twitter (52:00) and Grantland/Linsanity (1:12:00). Learn more about your ad choices. Visit podcastchoices.com/adchoices

2 Des 20151h 16min

HBO's Bill Simmons talks to Cousin Sal about Sunday night's controversial Pats-Broncos game, the Thanksgiving games (25:00 mark), Week 13 NFL picks (30:00), NFC East quagmire (40:00), Adam Carolla (53:00), Mike Tomlin's crazy coaching (1:02) and 'Creed' (1:09--Spoiler Alert!). Learn more about your ad choices. Visit podcastchoices.com/adchoices

30 Nov 20151h 15min

HBO's Bill Simmons talks to 'Creed' star Michael B. Jordan about his bond with Carl Weathers (4:00 mark), the 'Rocky' franchise (7:00), Stallone's Oscar-worthy performance (13:00), Cotto-Canelo ringside reactions (21:00), mimicking top flight acting talents (28:00), 'The Wire' vs. 'Friday Night Lights' (34:00), Ryan Coogler's creative touch on 'Creed' (44:00), future projects (54:00) and a modern Rom-Com starring alongside Jennifer Lawrence (1:04:00). Learn more about your ad choices. Visit podcastchoices.com/adchoices

25 Nov 20151h 7min

HBO's Bill Simmons discusses NBA vs. college coaches (2:00 mark), Stephen Curry's mastery of chaos (8:00), Spurs/GSW (13:00), Spurs' ceiling(21:00), Doc Rivers/Clips (29:00), NBA innovations (39:00), Houston/OKC (47:00) and best rookies (56:00) with esteemed NBA gambler Haralabob Voulgaris. Then, Joe House talks Chinese food (1:06:00), Thanksgiving NFL picks (1:12:00) and Ben Simmons (1:22:00) Learn more about your ad choices. Visit podcastchoices.com/adchoices

24 Nov 20151h 30min