‘Obsession’ With Bill Simmons, Chris Ryan, and Joanna Robinson
July 28, 2026 · Obsession (2025) · Horror · 1:56:59 · ▶ Listen on Spotify
Bill's crazy lady movies by decade
Tiered list · Bill Simmons · ▶ 30:55
70s
- ·Play Misty for Me (1971)▶ 30:55
80s
- ·Fatal Attraction (1987)▶ 31:17
90s
- ·Disclosure (1994)▶ 31:29
2000s
- ·Unfaithful (2002)▶ 31:53
Joanna's 21st century Nice Guy (TM) movies
Unranked list · Joanna Robinson, Chris Ryan · ▶ 32:47
- ·Eternal Sunshine of the Spotless Mind (2004) · Joanna Robinson▶ 32:47
- ·500 Days of Summer (2009) · Joanna Robinson▶ 32:49
- ·Ruby Sparks (2012) · Joanna Robinson▶ 32:50
- ·Lars and the Real Girl (2007) · honorable mention · Chris Ryan▶ 33:07
- ·Her (2013) · Joanna Robinson▶ 33:16
- ·Ex Machina (2014) · Joanna Robinson▶ 33:17
- ·Companion (2025) · Joanna Robinson▶ 33:18
- ·Don't Worry Darling (2022) · Joanna Robinson▶ 34:25
- ·Promising Young Woman (2020) · Joanna Robinson▶ 33:33
- ·Gone Girl (2014) · Joanna Robinson▶ 33:35
- ·Garden State (2004) · Joanna Robinson▶ 34:37
Categories
Would Roger Ebert Have Liked This Movie
Bill Simmons▶ 51:11Instead of asking about Ebert, Bill asked Claude to write a fake review of 'Obsession' in his own voice, calling it a 'full Simmons reversal' praising the film as the best horror movie of the year; he seems half-amused, half-unsettled by AI mimicking him.
Joanna Robinson▶ 51:37Says she would have made the same 'Lifetime movie' joke about the title, confirming the AI captured Simmons' voice accurately.
Most Rewatchable Scene
Bill Simmons▶ 58:58Bear sneaking out to see Sarah, culminating in Nikki smashing Sarah's head through the window - his number one pick
Chris Ryan▶ 1:00:38The dinner/incest monologue scene (Gretel/Hansel poem reading) where Nikki reveals she's joking, followed by her reaction to 'kiss the person you're left with'
Craig Horlbeck▶ 1:00:54The scene where Bear wakes up in the middle of the night and Nikki is sitting awake in the corner with the flower pot
Joanna Robinson▶ 55:50The scene where Nikki is creeping in the corner of the bedroom, moving unnaturally like a Pink Panther creep out of the shadows
Great Shot Gordo Award
Bill Simmons▶ 1:11:17References the Halloween-style shot where a character comes out after seeing friends butchered, realizing Michael Myers is still in the house, and his white face slowly emerges in the background
Joanna Robinson▶ 1:11:38The Hereditary shot where the camera stays fixed in a corner and you can't find the character in frame, creating dread about where she is
Butch's Girlfriend Award
Bill Simmons▶ 1:16:53The 'Wish Willow' phone call scene where the customer service rep, Nikki, is heard screaming from hell in the background while the guy tries to alter/cancel his wish
Chris Ryan▶ 1:16:39Initially agreed Ian/Cooper Tomlinson could be an obvious pick but pushed back, then sided with Joanna against Bill on keeping the screaming in the Wish Willow scene
Craig Horlbeck▶ 1:19:10The MPAA/ratings board being 'the worst' for forcing cuts (removing head smashes) from the violent brick scene with Sarah to get an R rating instead of NC-17
Stephen A. Smith Hottest Take Award
Bill Simmons▶ 1:23:57If Timothée Chalamet plays Bear (in a Bear vs. wilderness/horror scenario referencing Revenant-style survival), it would be the greatest horror movie of all time; also jokes he could keep casting Chalamet in everything instead of more Dune movies
Chris Ryan▶ 1:27:05Bear never actually loved Nicky — he only falls for her when she rejects him (cracks the wish), revealing he was never emotionally committed to her even after 'damning' her
Joanna Robinson▶ 1:25:03Nicky doesn't deserve what happens to her, but it's suspicious/telling that she has no real friend network to intervene in her life ('like an Aaron Rodgers thing, no one knows this girl')
Casting What-Ifs
Bill Simmons▶ 1:28:34Notes Barker originally wanted to cast himself as Bear, talked himself out of it, and Thomason played Bear in setup scenes before being replaced by Andy Richter's lookalike. Also proposes alternate 'Boston movie' casting: young Casey Affleck (Goodwill Hunting era) as Bear and Blake Lively (her character in The Town) as Nicky.
Chris Ryan▶ 1:29:02Notes Cooper and Curry (Barker) have real TV/sketch comedy backgrounds (e.g., It's Always Sunny); also picks the female crystal shop worker over the male as his favorite casting choice in that scene.
Half-Assed Internet Research
Bill Simmons▶ 1:34:52Says this movie (Obsession) feels bigger than Blair Witch in terms of return on investment (500x budget)
Chris Ryan▶ 1:35:09Compares the film to Blair Witch/indie horror lineage but is skeptical it will have the same lasting cultural impact in 10 years
Craig Horlbeck▶ 1:34:45Blair Witch made $250M on a $500K budget; notes the internet helped spread Obsession's word-of-mouth in a way Blair Witch couldn't in 1999
Joanna Robinson▶ 1:34:04Trivia: Michael/Mackenzie got the role because he and the other actor had no chemistry in their audition, per casting director's note
Picking Nits
Bill Simmons▶ 1:38:07Multiple nitpicks: low budget shows in the dead cat and Sarah's mannequin-like corpse; Bear is a terrible pet/cat owner who leaves for two days then blithely moves on; Bear still wants the wish granted even after trying to alter it; and no friends intervene as Nikki spirals, which is the biggest nitpick overall.
Chris Ryan▶ 1:37:05Bear doesn't insist Nikki get her bottle stab wounds treated at the hospital, and no one at the party calls 911 despite the obvious warning signs; also questions how Sarah's fake leftover sandwich could look so convincing.
Joanna Robinson▶ 1:37:39Nitpicks the amount of prep work the killer supposedly did after Sarah's death (getting the gun from the safe, recreating tattoos/haircut in Sharpie) in a short amount of time, and notes no one intervenes despite things clearly being 'fucked up.'
Sequel/Prequel/Limited Series/Remake
Bill Simmons▶ 1:42:20Wants a prestige anthology series where each episode is about a wish (inspired by 'Wish' reboot idea); also pitches a sequel where Ian didn't die, becomes a billionaire but all his friends are dead, and someone else (maybe Andy Richter) finds and spends his money
Chris Ryan▶ 1:43:14Notes there will inevitably be an 'Obsession'-style project since there's too much money at stake; mentions the actor (referenced as 'him') already making a ghost hunter movie with Cooper Tomlinson and Aaron Paul, and is supposedly set to make Texas Chainsaw Massacre next
Is This Movie Better With
Bill Simmons▶ 1:44:22Lists potential utility players (Wayne Jenkins, Zane Lowe, Robert Evans, Dr. Charles Nichols) and praises Chris's Bernthal bit as 'astounding work'; had considered Tony Romo but passes due to his real-life issues
Chris Ryan▶ 1:43:51Pitches Jon Bernthal as the customer service voice, playing 'King Menelaus' doing a bit about 'freaky Nicky' (Helen of Troy riff)
Joanna Robinson▶ 1:43:34Compliments the bit ('that's a good one'), shifts to reminiscing about Bernthal sparring with Kevin Feige at Comic-Con rather than making a new pick
Probably Unanswerable Questions
Bill Simmons▶ 1:46:41Agrees the eyes/gun quote is crazier; on the cat possession theory, says it's probably not true but likes the idea, thinks the movie would be dumber if true, and jokes it might just be a horror-comedy idea the filmmakers abandoned
Bill Simmons▶ 1:50:00Speculates a sequel/prequel could explore what happened to other 'One Wish Willow' buyers, and wonders if Wayne Jenkins' crew found Ian's billion dollars and pocketed it
Chris Ryan▶ 1:46:31Says the Heat quote (ripping eyes out and shoving barrel gun into himself) is crazier than the 'no sperm left if I was a Bulls fan' line; also wishes smoking cigarettes was actually healthy
Chris Ryan▶ 1:49:12Thinks the crystal shop employees are somewhat complicit since they confirm the wish 'totally works' without warning about fine print; also flags the scene breaking from Bear's POV to show Nikki as a plot inconsistency
Craig Horlbeck▶ 1:48:14Would wish for Aaron Rodgers to win MVP this year and for the Chargers/Rodgers to stay healthy
Joanna Robinson▶ 1:46:55Says she'd be too scared to make any wish given how many wish-gone-wrong movies she's seen; compares wish rules to Aladdin (can't bring back the dead, can't force love); believes the crystal shop saleswoman isn't evil, just believes people who fall for the wish deserve what's coming
Coach Finstock Life Lesson
Bill Simmons▶ 1:50:40The lesson that 'you can't pray for someone to fall in love with you, it's bad karma' — and that sometimes it's okay to be in the friend zone
Best Double Feature
Bill Simmons▶ 1:50:55Play Misty for Me paired with Single White Female (obsessive relationship theme)
Chris Ryan▶ 1:51:24Mentions 'milk and cereal' comparison and references Curry's, but pick is unclear from transcript
Who Won the Movie
Bill Simmons▶ 1:51:38Calls it a tie between Mia Goth (Indy/Curry) and MaXXXine/actress vs. director Osgood Perkins, comparing it to Sixth Sense debate; ultimately leans toward the actress (Indy) having a star-making moment like Scarlett Johansson in Lost in Translation, but says it's genuinely a tie between director and actress
Craig Horlbeck▶ 1:52:17Frames it as 'who would you rather be' professionally; argues the actress's risk is higher since one bad movie could end her run, while the director could survive a couple bad films more easily, but ultimately credits the actress's performance as career-making
Joanna Robinson▶ 1:52:36Agrees the actress (Indy) carries more risk going forward than the director, since her next roles could make or break her, while the director likely has more cushion
Movies Referenced (62)
Hereditary (2018)
8 mentions · Bill Simmons, Chris Ryan, Joanna Robinson▶ 8:35IMDb ↗Lb ↗
Heat (1995)
6 mentions · Bill Simmons, Chris Ryan, Joanna Robinson▶ 0:28IMDb ↗Lb ↗
Can't Hardly Wait (1998)
4 mentions · Joanna Robinson, Chris Ryan, Bill Simmons▶ 17:05IMDb ↗Lb ↗
Cape Fear (1991)
3 mentions · Joanna Robinson, Bill Simmons▶ 1:08:49IMDb ↗Lb ↗
Directors Referenced (2)
Christopher Nolan
1 mentions · Joanna Robinson · Known for Tenet, Interstellar, Inception▶ 1:09:55IMDb ↗Lb ↗
Michael Mann
1 mentions · Chris Ryan · Known for The Insider, Collateral, The Last of the Mohicans▶ 11:23IMDb ↗Lb ↗
Actors Referenced (19)
Curry Barker
17 mentions · Bill Simmons, Chris Ryan, Joanna Robinson · Known for Obsession▶ 8:45IMDb ↗Lb ↗
Andy Richter
5 mentions · Bill Simmons, Craig Horlbeck · Known for Elf▶ 1:02:48IMDb ↗Lb ↗
Samantha Morton
4 mentions · Chris Ryan, Joanna Robinson · Known for Minority Report, Synecdoche, New York, In America▶ 29:17IMDb ↗Lb ↗
LeBron James
2 mentions · Bill Simmons · Known for Trainwreck, Hustle▶ 0:19IMDb ↗Lb ↗
Michael Douglas
2 mentions · Bill Simmons · Known for Wall Street, Behind the Candelabra, Romancing the Stone▶ 31:37IMDb ↗Lb ↗
Aaron Paul
1 mentions · Bill Simmons · Known for El Camino, Need for Speed▶ 1:43:23IMDb ↗Lb ↗
Anne Hathaway
1 mentions · Chris Ryan · Known for The Dark Knight Rises, Rachel Getting Married▶ 30:20IMDb ↗Lb ↗
Austin Abrams
1 mentions · Bill Simmons · Known for Paper Towns, Weapons, Do Revenge▶ 1:30:15IMDb ↗Lb ↗
Betty Gabriel
1 mentions · Bill Simmons · Known for Get Out, Upgrade▶ 55:41IMDb ↗Lb ↗
Donald Trump
1 mentions · Bill Simmons · Known for Home Alone 2: Lost in New York▶ 1:12:30IMDb ↗Lb ↗
Harrison Ford
1 mentions · Bill Simmons · Known for Raiders of the Lost Ark, Star Wars: Episode IV - A New Hope, The Fugitive▶ 1:23:57IMDb ↗Lb ↗
Jason Blum
1 mentions · Joanna Robinson · Known for Get Out▶ 44:39IMDb ↗Lb ↗