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‘Someone to Watch Over Me’ With Bill Simmons and Chris Ryan

April 29, 2025 · Someone to Watch Over Me (1987) · Crime · Drama · Romance · 1:30:30 · ▶ Listen on Spotify

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Casting What-Ifs

Bill Simmons▶ 21:54Lorraine Bracco — Discusses Lorraine Bracco's casting and mentions she was unknown before this role, then discusses Mimi Rogers' casting and mentions she lost Face/Off to Sharon Stone as another casting what-if
Bill Simmons▶ 1:02:52Keyed on the big real what-if: Sharon Stone screen-tested for Claire (Mimi Rogers got it, then the roles flipped four years later with Basic Instinct) — with Stone as Claire it's 'a completely different movie... he's never going back'; also floated Demi Moore circa '93-'94 Disclosure-range, Kidman post-Days of Thunder, and endorsed Chris's Chastain idea; noted Mimi Rogers tested for both female parts.
Chris Ryan▶ 26:16Lorraine Bracco — Agrees that Bracco was great casting choice and discusses how Mimi Rogers could have had a bigger career, comparing her potential to Susan Sarandon
Chris Ryan▶ 1:04:16His recasts: Jessica Chastain (early-to-mid 2010s) as Claire — the pick Bill called 'really good' — after working through Susan Sarandon (decided she'd fit Ellie, not Claire) and suggesting Geena Davis or Melanie Griffith as Ellie ('you need somebody more Queens').

Most Rewatchable Scene

Bill Simmons▶ 34:18Opening credits with Sting, opening cop party, walking around Claire's apartment when Berenger gets lost and ends up in the closet, going to the Guggenheim and tie shopping
Chris Ryan▶ 36:23Agrees with the cop party scene, noting the storytelling about the promotion and how it goes from afternoon to 2am

What's Aged the Best

Bill Simmons▶ 48:32Multiple picks including: cop daughters who marry cops, cops calling wives 'the old lady', Lorraine Bracco scenes knowing Goodfellas is coming, two-way mirrors for perp ID, Mike's 80s Jets sweatshirt with collar, New York pronunciation of 'idea' as 'idear', and Barringer's bachelor friend's apartment with bunk beds
Chris Ryan▶ 48:01Koontz the cop having a little stud earring - thinks guys should just start wearing them again

Dion Waiters Award

Bill Simmons▶ 51:11Barringer on the New York 80s subway standing up with flickering lights
Chris Ryan▶ 51:05Barringer on the New York 80s subway standing up

Den of Thieves Benihana Award

Bill Simmons▶ 51:28The New York City apartment

Butch's Girlfriend Award

Bill Simmons▶ 55:29The last 10 minutes
Chris Ryan▶ 55:47Agrees with criticism of the last 10 minutes, particularly questioning the illogical plot decisions and character strategies

What's Aged the Worst

Bill Simmons▶ 57:20Claire having a painting of herself, fake punch sound effects, Jerry Orbach's over-the-top Oscar-baiting performance in hospital scene, and Venza's implausible party infiltration while being a wanted fugitive
Chris Ryan▶ 57:59The fake punch sound effects and inappropriate workplace behavior (captain asking personal questions about Mike's relationship)

Stephen A. Smith Hottest Take Award

Bill Simmons▶ 59:51This movie had all the tools to be the greatest erotic thriller of all time, even better than Fatal Attraction as a blueprint
Chris Ryan▶ 59:10Venza is the best thing that ever happened to Mike and Ellie - his dangerous entrance saved them from a life of recrimination and financial stress, showed them what's important, and reinvigorated their relationship

Apex Mountain

Bill Simmons▶ 1:09:16Tom Berenger — Berenger - Platoon; Mimi Rogers - this movie; Bracco - Goodfellas; Arturus - Fugitive; Ridley Scott - Gladiator; Guggenheim museum in movies - this movie; Rich hot socialite characters - uncertain between this movie and Talented Mr. Ripley
Chris Ryan▶ 1:09:19Tom Berenger — Agreed on Berenger - Platoon; Queens movies - Coming to America is the best; Rich hot socialite characters - Talented Mr. Ripley (Gwyneth Paltrow's Marge)

Picking Nits

Bill Simmons▶ 1:13:51Venza's legal status is confusing (unclear if he's out on bail or case is closed); Claire would never be with Neil (he's not compelling enough); Claire saying 'I have to go for a pee' is too crude for her character; Joey should have murdered Claire in the bathroom instead of just threatening her
Chris Ryan▶ 1:13:37Venza's motivations and plan are unclear; witness protection wouldn't work the way shown (Claire would be in secure location, not her apartment); Joey should have just killed Claire in the bathroom instead of threatening her

Is This Movie Better With

Bill Simmons▶ 1:19:12Doris Burke — Doris Burke (DB) - suggests her commenting on Mike walking the streets of New York battling his moral conscience about marriage versus adultery
Chris Ryan▶ 1:18:37Wilford Brimley — Wilford Brimley in the firm - delivers an elaborate crossover bit mixing The Fugitive with A Few Good Men references

Probably Unanswerable Questions

Bill Simmons▶ 1:19:35How loaded was Claire? (family money, parents died in helicopter crash, inherited wealth). Claire as one of the great catches in movie history? What do Claire's next three boyfriends look like after this trauma?
Chris Ryan▶ 1:19:40Claire has generational wealth like the Gettys, had a bad relationship with Neil as rebound, would be difficult to approach, next boyfriends would be Italian count or going for the stars after nearly being murdered

Best Double Feature

Bill Simmons▶ 1:25:21Black Widow — Someone to Watch Over Me paired with Black Widow

Who Won the Movie

Bill Simmons▶ 1:26:13Mimi Rogers
Chris Ryan▶ 1:26:05Ridley Scott — Ridley Scott (the director)

Movies Referenced (38)

Platoon (1986)

7 mentions · Chris Ryan, Bill Simmons▶ 16:55IMDb ↗Lb ↗

Goodfellas (1990)

6 mentions · Bill Simmons▶ 22:46IMDb ↗Lb ↗

Black Widow (2021)

4 mentions · Bill Simmons▶ 1:25:11IMDb ↗Lb ↗

Alien (1979)

3 mentions · Bill Simmons, Chris Ryan▶ 14:19IMDb ↗Lb ↗

Blade Runner (1982)

3 mentions · Bill Simmons, Chris Ryan▶ 14:16IMDb ↗Lb ↗

Body Heat (1981)

3 mentions · Bill Simmons, Chris Ryan▶ 7:52IMDb ↗Lb ↗

Fatal Attraction (1987)

3 mentions · Bill Simmons▶ 8:35IMDb ↗Lb ↗

Jagged Edge (1985)

3 mentions · Bill Simmons, Chris Ryan▶ 1:25:02IMDb ↗Lb ↗

Legend (2015)

3 mentions · Bill Simmons▶ 14:18IMDb ↗Lb ↗

Basic Instinct (1992)

2 mentions · Bill Simmons▶ 1:02:59IMDb ↗Lb ↗

Don't Say a Word (2001)

2 mentions · Chris Ryan, Bill Simmons▶ 58:34IMDb ↗Lb ↗

Heat (1995)

2 mentions · Chris Ryan, Bill Simmons▶ 38:40IMDb ↗Lb ↗

Directors Referenced (4)

Ridley Scott

20 mentions · Bill Simmons, Chris Ryan · Known for The Martian, Blade Runner, Thelma & Louise▶ 10:31IMDb ↗Lb ↗

Iyi Tubi

11 mentions · Bill Simmons, Chris Ryan · Known for Ex Machina, World War Z▶ 2:12IMDb ↗Lb ↗

Sean Penn

3 mentions · Bill Simmons · Known for Mystic River, 21 Grams, Dead Man Walking▶ 14:08IMDb ↗Lb ↗

Tony Scott

2 mentions · Chris Ryan · Known for Domino, Unstoppable, True Romance▶ 13:08IMDb ↗Lb ↗

Actors Referenced (61)

Mimi Rogers

37 mentions · Bill Simmons, Chris Ryan · Known for Ginger Snaps, Lost in Space▶ 6:25IMDb ↗Lb ↗

Lorraine Bracco

17 mentions · Bill Simmons, Chris Ryan · Known for Goodfellas, Medicine Man▶ 6:33IMDb ↗Lb ↗

Tom Berenger

8 mentions · Bill Simmons, Chris Ryan · Known for Platoon, Inception, The Big Chill▶ 6:52IMDb ↗Lb ↗

Tom Cruise

7 mentions · Bill Simmons, Chris Ryan · Known for Top Gun, Mission: Impossible II, Minority Report▶ 23:32IMDb ↗Lb ↗

Steve Winwood

6 mentions · Bill Simmons · Known for Flight of the Phoenix, Spider-Man: Homecoming▶ 46:22IMDb ↗Lb ↗

Roberta Flack

5 mentions · Bill Simmons · Known for The Man from U.N.C.L.E., Play Misty for Me▶ 29:32IMDb ↗Lb ↗

Sharon Stone

4 mentions · Bill Simmons, Chris Ryan · Known for Basic Instinct, Casino, The Quick and the Dead▶ 25:30IMDb ↗Lb ↗

Susan Sarandon

4 mentions · Chris Ryan, Bill Simmons · Known for Thelma & Louise, Dead Man Walking▶ 26:13IMDb ↗Lb ↗

Jagged Edge

3 mentions · Bill Simmons, Chris Ryan · Known for Bad Company, Big Momma's House, Hardball▶ 1:25:02IMDb ↗Lb ↗

Jessica Chastain

3 mentions · Bill Simmons · Known for Zero Dark Thirty, Crimson Peak, Molly's Game▶ 28:09IMDb ↗Lb ↗

Mary Astor

3 mentions · Chris Ryan, Bill Simmons · Known for The Maltese Falcon, Meet Me in St. Louis▶ 52:14IMDb ↗Lb ↗

Michael Douglas

3 mentions · Bill Simmons, Chris Ryan · Known for Wall Street, Behind the Candelabra, Romancing the Stone▶ 25:58IMDb ↗Lb ↗

Writers Referenced (5)

Roger Ebert

2 mentions · Bill Simmons▶ 30:56IMDb ↗Lb ↗

Taylor Sheridan

2 mentions · Chris Ryan · Known for Hell or High Water, Wind River▶ 19:57IMDb ↗Lb ↗

Tony Behringer

2 mentions · Chris Ryan, Bill Simmons · Known for No Hard Feelings, Draft Day▶ 31:02IMDb ↗Lb ↗

George Gershwin

1 mentions · Bill Simmons · Known for Manhattan, Venom: Let There Be Carnage▶ 29:16IMDb ↗Lb ↗

Howard Franklin

1 mentions · Bill Simmons · Known for The Name of the Rose▶ 30:19IMDb ↗Lb ↗