Sharp or Square: Academy Awards Betting Preview

Podcast: Sharp or Square
Episode: Academy Awards Betting Preview with Michael Lasker
Date: March 13, 2026
Host(s): Chad Millman & Simon Hunter
Guest: Michael Lasker (Hollywood manager and Oscar savant)

Episode Overview

This special episode of Sharp or Square veers from the usual NFL and sports betting content to provide a deep-dive betting preview for the 98th Academy Awards. Chad Millman and Simon Hunter welcome back famed Hollywood insider Michael Lasker to break down Oscar odds, discuss narratives behind the top films and performances, and offer listeners tactical advice for both casual Oscar pools and the legal betting markets. The conversation blends film analysis, inside-Hollywood wisdom, and betting insight, creating a comprehensive guide for anyone looking to gain an edge on Oscars night.

Key Discussion Points & Insights

1. Oscars as a Betting Market

• Difficulty of Profitable Betting (09:00–10:20):
  Lasker points out that Oscar betting is tougher than sports due to information leakage (precursor awards, expert consensus) and the sheer volume of odds-on favorites. The suggestion: your work Oscar pool has more edge than a regulated sportsbook.

  • "There's more money, in my mind, to be made in the Oscar pool inside your living room than there is online because there's so much information out there." — Lasker (08:25)

• Parlay Strategies (32:20–32:41):
  Simon shares how he parlayed Oscars selections with NFL bets to improve odds, showing the increasing sophistication of entertainment betting strategies.

2. Major Film Showdown: “One Battle After Another” vs. “Sinners”

The Race

• Overview (11:30–13:00):
  It's a two-picture race, with “One Battle After Another” (PTA) and “Sinners” (Ryan Coogler) leading both critical and commercial conversation.

• Genre and Oscar Sensibility (13:58–18:17):
  Simon is shocked at "Sinners"—a vampire film—being a frontrunner for Best Picture, citing traditional Oscar disinterest in genre fare.

  • "This is a classic, very dumb movie where they couldn't figure out to end it...Would never in a million years...have bet it to even be nominated at the Oscars." — Simon (12:45)

Analysis of Appeal

• Why “Sinners” Became an Oscar Contender (13:58–18:17):
  Lasker offers a deep analysis: it's about commercial and cultural impact, Coogler's auteur rise, the film’s allegorical layers (race, history, Irish and African-American experience), and Michael B. Jordan’s dual-role performance.

  • “He made it feel new again because it was new in the eyes of the characters...it was also a story about the plight of African Americans who still can’t get ahead.” — Lasker (15:30)

• The Power of Narrative and Timing:
  Both hosts and Lasker note how the Academy “cycles” into rewarding new generations of filmmakers when their body of work matures—Coogler now, PTA finally.

  • "Sometimes filmmakers...grow into the people they become, and then the Academy and the business takes note." — Lasker (23:32)

Commercial vs. Critical Success (27:25–29:27)

• For once, blockbusters are favored instead of penalized. Chad is particularly pleased that “One Battle After Another” and “Sinners” are populist hits as well as critical darlings.
  • "Usually that is, to your point, a knock on them winning. And yet that is going to be something that happens." — Chad (27:25)

3. Key Category Deep Dives

Best Picture & Director (28:49–32:20)

• Lasker's Prediction:
  • “One Battle After Another” to win Best Picture and Director (PTA), with “Sinners” picking up key acting and screenplay Oscars.
  • "As of now I have One Battle winning six and Sinners winning four." (28:56)
  • "I just think it's his [PTA's] moment." (31:58)

Best Actor (33:57–37:22)

• Biggest Wild Card:
  • Michael B. Jordan is now favorite, but Lasker emphasizes anyone could win—2016 Mahershala Ali as a comp.
  • Simon notes he bet Jordan when he was a long shot.
• Narrative Analysis:
  • The Academy often delays awards for “pheno” young actors like Chalamet (Timmy), preferring to reward breakout mature performances.
• Notable Quote:
  • "This is the one where literally I can make the argument for all five guys winning." — Lasker (34:14)

Best Actress (Hamnet, Begonia, If I Had Legs I’d Kick You) (47:00–51:48)

• Jesse Buckley in “Hamnet”:
  • Lock for the award — praised for emotional range, with notable trivia on her process and personal life enhancing the discussion.
    • "Actors...you don't have to have been in a concentration camp to be in Schindler's List." — Lasker (51:48)
  • Chad highlights the sheer emotional brutality of the film and Buckley’s one-take scream scene.
    • "She did that multiple times. And that was the third take...unscripted, let it go...and that's the one that they kept." — Chad (50:48)
• Rose Byrne’s Snub:
  • Chad questions why Rose Byrne isn’t getting more buzz.
  • Lasker: Hollywood views her dominance as "arrival", Buckley’s as “moment”.

Best Supporting Actress (54:07–58:12)

• Amy Madigan (“Weapons”) vs. Yona Taylor (“One Battle After Another”):
  • Madigan, a veteran, is the favorite, but it’s close—anyone could win.
  • "I think she's gonna win for a couple reasons. The supporting actor races are sometimes where they give it to a villain—which also is gonna help Sean Penn...she's the villain of that movie by a long stretch." — Lasker (55:20)
  • The category’s historical unpredictability is discussed at length.

4. Notable Quotes & Moments

Lightning Oscar Trivia Rounds

• Throughout, Chad peppers Lasker with rapid-fire Oscar pop quizzes, which he nails, reinforcing his “savant” rep.
  • "The best actor in 1982 for the film year...Ben Kingsley for Gandhi..." (11:02)
  • "2002, the best picture winner is Chicago. And the other nominees..." (58:44)

Film Critique: “Marty Supreme”

• Chad loathes the “one note” style, despite its period and subject matter:
  • "I didn't love Marty Supreme. I just didn't think it was that good of a movie. I thought it was self indulgent. I thought it was too long. I thought that it was one note." — Chad (37:22)
• Lasker offers a more measured, but ultimately similar, assessment.

Oscars as Narrative

• Multiple times, Lasker and the hosts stress that Oscars are as much about industry and cultural narrative as about quality.
  • "You gotta ask: what's the story the next day?" (28:49)

Timestamps of Important Segments

• Intro & Hoosiers Banter: 02:38–06:01
• Michael Lasker Joins, Oscars Year-in-Review: 07:29–09:24
• Oscar Betting Market Realities: 09:24–11:31
• Pop Quiz #1 - 1982 Oscars: 10:49–11:31
• Best Picture Race Analysis (One Battle vs Sinners): 11:31–18:17
• Modern Era of Hollywood & Directors: 18:17–24:04
• Biggest Oscar Trends, Commercial Success Discussion: 27:25–28:47
• Direct Category Predictions (Picture/Director/Acting): 28:47–37:22
• Best Actress Deep Dive (Buckley, Byrne): 47:00–52:03
• Supporting Actress Wild Card Discussion: 54:07–58:12
• Lightning Rounds - Oscar Nominee Pop Quizzes: Throughout (notably at 10:49, 52:17, 58:27)
• Wrap Up, Final Prep for Betting: 58:12–60:45

Tone & Takeaways

• Tone: Knowledgeable, witty, conversational, peppered with friendly Hollywood-insider humor and sharp, self-aware commentary on the Oscars’ quirks.
• Takeaway: For serious Oscar pools and bettors, focus on “One Battle After Another” for Best Picture/Director, Michael B. Jordan as rising Best Actor favorite, and Jesse Buckley as a best actress lock. Categories like Best Supporting Actress remain highly volatile—and often offer the only real ‘value’ for betting.

Quick Bet Favorites (as predicted on the show)

• Best Picture/Director: “One Battle After Another” (Director: Paul Thomas Anderson)
• Best Actor: Michael B. Jordan (“Sinners”)
• Best Actress: Jesse Buckley (“Hamnet”)
• Best Supporting Actress: Amy Madigan (“Weapons”), but watch for Teyana Taylor as a live dog.

Memorable Quotes

• "This is a classic, very dumb movie where they couldn't figure out to end it...[Sinners]" — Simon (12:45)
• "There's more money...in the Oscar pool inside your living room than there is online..." — Lasker (08:25)
• "I just think it's his [PTA's] moment...I don't think he's going to be denied." — Lasker (31:55)
• "She just lets it go full, like, scream that honestly makes you want to disappear into a dark, dark hole." — Chad (50:48)
• "This is the one where literally I can make the argument for all five guys winning." — Lasker (34:14)
• "Supporting actor and actress categories are where the Oscars can get a little funky." — Lasker (55:20)

For listeners:

If you want a smart, incisive, and occasionally irreverent edge on this year’s Oscars—whether betting real money or just aiming for bragging rights—this guide has you covered.