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The Brothers Sinatra Podcast

The Brothers Sinatra Podcast

Written by: The Brothers Sinatra
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About this listen

The only Chicago-based podcast featuring two real swingin' brothers talking about media. Jack and Tyler Sinatra discuss Movies, TV, Music, Video Games, and more.The Brothers Sinatra Art
Episodes
  • Sinatra Streams: Why is Sydney Sweeney in Ron Howard's 'Eden'?
    Feb 16 2026

    Jack and Tyler discuss Ron Howard's 'Eden' released in 2024 starring Jude Law, Vanessa Kirby, Sydney Sweeney, Daniel Brühl, and Ana de Armas.


    For more Brothers Sinatra content go to https://veryentertaining.biz/


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    2 hrs and 20 mins
  • Sinatra Classics: Catherine O'Hara is every community theater actor in Christopher Guest's 'Waiting for Guffman'
    Feb 9 2026

    Jack and Tyler discuss Christopher Guest's 1996 mockumentary and ensemble comedy classic, 'Waiting for Guffman'.

    Sinatra Stats (6:18)

    Top 3 Christopher Guest Movies (17:15)

    Top 3 Catherine O'Hara Performances (26:18)

    **SPOILERS** (31:26)

    Sinatra Summaries (32:08)

    Nothing But the Best (35:59)

    Demerits (1:10:52)

    Questions (1:18:55)

    Send in the Clowns, Funniest Part (1:30:30)

    The Way You Look Tonight, Best Fit (1:35:01)

    Casting Crooners (1:36:37)

    The Best is Yet to Come, Sequel Ideas (1:38:48)

    Something Stupid (1:42:38)

    Some Like it Hot, Hottest Take (1:51:35)

    Strangers in the Night, Best Cameo/Feature (1:57:25)

    Me and My Shadow, Best Brothers/Sisters/Companions (2:00:56)

    Chariman of the Board, Winner (2:02:05)

    Rating out of Five Franks (2:06:23)

    Next Week (2:08:16)

    For more Brothers Sinatra content see https://veryentertaining.biz/

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    2 hrs and 12 mins
  • Sinatra Classics: Bill Murray's brilliance in 'Groundhog Day'
    Feb 2 2026

    It's the first edition of Sinatra Classics where Jack and Tyler delve into Harold Ramis' venerated Bill Murray vehicle, Groundhog Day. Would Phil Connors get canceled nowadays? Is Rita a catch? Too early for flapjacks? All of this and more on a special holiday pod.

    After a brief introduction...

    Groundhog Day overview (7:35)

    Other time loop narratives (21:11)

    *SPOILERS* (30:25)

    Sinatra Summaries (31:10)

    CATEGORIES

    Walkthrough (33:35)

    Nothing But the Best, Best Parts (59:00)

    Demerits (1:06:02)

    Questions (1:13:36)

    Send in the Clowns, Funniest Part (1:27:04)

    The Way You Look Tonight (1:35:02)

    Casting Crooners (1:38:00)

    The Best is Yet to Come, Sequel Ideas (1:41:53)

    Somethin' Stupid, Random Facts (1:47:27)

    Some Like it Hot, Hottest Take (1:54:10)

    Strangers in the Night, Features/Cameos (2:03:30)

    Me and My Shadow, Best Brothers (2:06:14)

    Chairman of the Board (2:08:22)

    Rating Out of Five Franks (2:10:04)

    Next Week Preview: Waiting for Guffman (2:12:40)

    For more Brothers Sinatra content check out https://veryentertaining.biz/




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    2 hrs and 15 mins
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