Broadway Breakdown: Deep Dive — CHICAGO (Movie) w/ Casey Balsham

Podcast: Broadway Breakdown
Host: Matt Koplik
Guest: Casey Balsham
Episode: Deep Dive: CHICAGO (Movie)
Date: January 15, 2026

Episode Overview

This episode of Broadway Breakdown offers an enthusiastic, no-holds-barred deep dive into the 2002 movie musical "Chicago." Host Matt Koplik is joined by comedian, podcaster, and Broadway lover Casey Balsham. Together, they break down what makes "Chicago" a perfect screen adaptation, dissect its casting history, the mechanics of its filmic musicality, its Oscar legacy, and its continued influence on Broadway and movie musicals. Expect passionate analysis, gossip, lots of laughter, and a smattering of four-letter words.

Key Discussion Points & Insights

Introductions & Banter ([00:35 - 03:06])

• Matt introduces Casey, highlighting the rise of her own podcast It's Broadway Bitch.
• They praise each other's work, establishing a fun, playful rapport ("Enough jerking each other off." [02:55])

Why "Chicago"? Personal Connections ([03:06 - 05:52])

• Casey’s love affair: Watched the film repeatedly in LA traffic during college; the soundtrack "kept me awake from getting in accidents." ([03:06])
• Matt's take: Calls the movie "perfect," with "no notes," and ranks it as the benchmark for modern movie musicals. ([03:35], [03:46])
• The soundtrack is dubbed a “no skip”—every song is essential.
• Discussion of how the parts don’t require "powerhouse" singers but strong character actors—a point they return to later.

Casting and Vocals: What Works, What Doesn’t ([05:52 - 10:12])

• "Renee Zellweger is not a Broadway singer — but it works for Roxy Hart." ([06:08])
• Roxy is a role that can be played by "semi non-singers," just like Sally Bowles in Cabaret ([07:04]).
• Velma is the singing role ("That was a pre-menopausal Chita doing it in 1975. You listen to her and you’re like, bitch can sing." [08:02])
• Sidebar on how women’s voices (and male voices) change with age; casting “over-qualified” or “under-qualified” singers can backfire.

Revisiting the Phenomenon ([10:12 - 13:13])

• Teasing upcoming “dreamcasting” segment, including the possibilities of gender-swapped casts and celebrities who could’ve starred.
• "Name a celebrity and at some point they were called." ([10:27])
• Hollywood’s infamously chaotic casting process for movie musicals is discussed.

Why Did Chicago Work? Lessons Unlearned ([12:04 - 14:54])

"There were a lot of lessons from Chicago that were not learned by Hollywood. And they don't learn lessons. Hollywood never learns lessons. [...] everyone involved has yet to make a movie musical as good as this since, by like a wide margin." — Matt ([12:04])

• Even Rob Marshall and others involved haven't replicated its success.
• Queen Latifah cited as the only “follow-up” success story (with "Hairspray").
• Casey investigated Marshall’s other movie musicals and found none nearly as remarkable.

Plot & Stage-to-Screen Origins ([14:54 - 25:04])

• Quick summary of the plot "as per Miramax" — fame, media, and corruption in the 1920s.
• Casey’s early experience: being a theatre major, singing and acting out the numbers with friends during the movie's Oscar season ([15:50]).
  • Humorous slip: Casey calls the Oscars "the Tonys." ([16:31])
• Casey only saw the musical after the movie; notes some live shows have become “drunk, half asleep” due to the long run. ([17:40])
• Matt's theatre nerd credentials: he saw the 1999 Broadway revival with Sharon Lawrence and Charlotte d’Amboise ([18:15]).
• Matt delivers a crisp, detailed history lesson:
  • The origins in Maureen Watkins' 1926 play; Bob Fosse and Gwen Verdon's pursuit of the rights ([19:22]).
  • Fosse’s heart attack led to a darker, more morbid original production (Gwen Verdon out, Liza Minnelli in temporarily) ([22:44]).
  • Only the 1996 Encores! revival (timed with the O.J. trial) made it a cultural juggernaut ([25:22]).

“Chicago” the Movie: The Long Road ([25:22 - 38:33])

• Marty Richards resisted Hollywood's overtures due to Fosse’s legacy.
• Multiple attempts: Fosse attempting with Goldie Hawn & Liza Minnelli, then Goldie and Madonna (swapping roles).
• Harvey Weinstein emerges; his involvement is explained (importantly, Matt clarifies Weinstein did not micromanage the film’s production).
• Rob Marshall’s arrival: His pitch that all songs emerge from Roxy’s mind is what finally “cracks” the adaptation ([34:52]).
  • "He comes up with the idea... She wants to be a performer and the only way she can understand the world is if everything's a musical number." ([34:44])

Wild Casting Stories ([35:16 - 44:59])

• Billy Flynn was first offered to John Travolta.
• Other rumored options: Hugh Jackman, Michael Jackson (nixed by Weinstein).
• Women who screen-tested for Roxy:
  • Mira Sorvino
  • Toni Collette ("There’s a giant conspiracy around Toni Collette not getting this role..." [38:45])
  • Christina Applegate, Jennifer Jason Leigh, Jennifer Aniston, Jodie Foster, Gwyneth Paltrow all rumored
• Catherine Zeta-Jones:
  • Was hosting a party, sang carols; offered Roxy (but wanted Velma). ([42:52])
  • "Does she sing ‘All That Jazz?’... well, that's who I want to play."
• Renee Zellweger’s casting: lunch with Marshall, performed “Over the Rainbow,” secured the part ([46:14]).

Perfect Movie, Perfect Ensemble ([44:59 - 49:58])

• Chicago had a $40M budget, filmed in Toronto.
• Opened to rave reviews, stellar box office, and Oscar glory.
• Matt and Casey celebrate the entire ensemble:
  • Queen Latifah as Mama Morton (originally tried for Kathy Bates)
  • John C. Reilly’s “desperate” pursuit for Amos Hart
  • Richard Gere’s unexpected but pitch-perfect Billy Flynn

Segment Highlights & Notable Quotes

Signature Numbers ([49:58 - 54:00])

• Favorite numbers:
  • Casey: "Cell Block Tango and ‘We Both Reached for the Gun’ ...the choreography throughout... it's magic.” ([49:58])
  • Matt: “Roxy, I think, is iconic and incredible and stunning and might be the best shot number of the movie.” ([53:27])
• On Catherine Zeta-Jones: “She’s like... she’s growling, she's crawling through the role. You're like, yes, this is exactly, perfectly cast for the two of them.” — Casey ([43:01])

How to Do a Movie Musical Right ([59:06 - 65:00])

“If you're gonna make a movie musical, you need to know this... establish a world where singing makes sense. You have to tell us how songs are going to be used...” — Matt ([59:57])

• Chicago establishes itself as a musical within moments, seamlessly blending narrative and numbers.
• Contrasts with "Dreamgirls," "Wicked," "West Side Story," and others that violate this “musical vocabulary” rule and/or have pacing problems.

Movie Musicals Since Chicago ([70:40 - 76:07])

• Matt and Casey bemoan how most post-Chicago stage-to-film adaptations haven’t matched its quality or learned its lessons.
• On the 2021 “West Side Story” and “Wicked” films: “Too much air, not as tight as they should be... especially in the first 30 minutes.” ([70:40])
• “Hairspray” (2007) and “Matilda” (Netflix) are cited as closer—Matilda is specifically championed as “fantastic and weird.”

The Oscars, Movie Bros, and Legacy Debates ([79:54 - 94:19])

• Matt scrutinizes the Oscar field of 2002, rewatching all five Best Picture nominees: “...anyone who says [LOTR] Two Towers... should have won Best Picture can fuck off.” ([80:54])
• On film-bro backlash: “What infuriates me even more is that they then go to bat for movie musicals after Chicago that are not nearly as good.” ([91:55])
• “Chicago” is the rare modern musical to triple-crown: “Good reviews, making money, and winning Oscars—and also still being relevant.” ([93:38])
• “Chicago is often a punching bag on movie podcasts... but it was the right winner.” ([79:54])

Acting, Performance, & Awards ([99:40 - 106:17])

• Richard Gere’s omission for Best Actor is called “an absolute joke.” ([56:46])
• Discussion of what counts as “award-worthy” acting; importance of “not seeing the work.”
  • “If I can't see the work, that's how I know it's good.” — Matt ([105:12])
• “Everyone in that movie, you don’t see the work. It’s just everyone is such a natural fit.” ([105:44])

Dream Casts & The Future ([106:28 - 110:17])

• Casey’s dream picks for a new “Chicago” film:
  • Roxy or Velma: René Rapp, Janelle Monáe
  • “Sheena Shay” (Vanderpump Rules) for Velma, “for something so terrible it would be fun”
  • Billy Flynn: Kate Hudson (for a gender-swapped twist)
  • Mama Morton: RuPaul
• Matt floats the idea of a 54 Below, all-queer Chicago concert, joking about a production with gender-bent casting called “Chicagays.” ([108:13])
• Both note: The continued passion surrounding “Chicago” is proof of its relevance.

Closing Moments

• Warm, humorous wrap-up with future podcast plugs, mutual invites, and giddy reflection on the film’s enduring adoration.
• Diva send-off request: “Bette Midler. Like Riri, she’s tiny and she’s here.” ([114:12])

Timestamps for Key Segments

• 03:06 — Casey’s personal history with Chicago
• 05:52 — On casting and vocal requirements
• 12:04 — Why Hollywood learned the wrong lessons from Chicago
• 19:22 — Deep history: from play to musical to movie
• 27:13 — Early movie adaptation attempts (Fosse, Goldie Hawn, Madonna)
• 34:52 — Rob Marshall’s breakthrough: Roxy’s mind as musical POV
• 42:52 — Catherine Zeta-Jones’s “All That Jazz” moment
• 46:14 — Renee Zellweger’s drunken “Over the Rainbow” lunch/audition
• 49:58 — Favorite numbers & visual standout moments
• 59:06 — How to make a movie musical work (the "Chicago rules")
• 70:40 — Why recent movie musicals miss the mark
• 79:54 — Matt vs. the “movie bro” anti-Chicago Oscar narrative
• 99:40 — Richard Gere’s acting vs. Daniel Day-Lewis/award show dynamics
• 106:28 — Dream casting of future Chicago productions
• 113:43 — Diva send-off (Bette Midler)

Memorable Quotes & Moments

• "Rub my nipples and call me pretty. Casey, what are we talking about today?" — Matt ([03:01])
• “Chicago is perfect. I have no notes on it.” — Matt ([03:46])
• "You don't need to be a proper singer for any of these roles." — Casey ([07:32])
• “I think it's wrong to cast people who are under-qualified vocally and overqualified vocally.” — Matt ([06:22])
• “So many people...still haven't been paid for their work. It's not all sunshine, rainbows and butt kisses on Broadway, everybody.” — Matt ([30:37])
• "She just looked at the whole thing as sin incarnate...wrote it as a satire." — Matt on Maureen Watkins ([20:07])
• “[The movie musical] needs pacing...numbers back to back for your first 40 minutes...that’s where Wicked and the new West Side Story fail.” — Matt ([68:49])
• “If you're gonna make a movie musical, you need to know this...establish a world where singing makes sense.” — Matt ([59:57])
• “Everyone in that movie, you don’t see the work...so much work to make it look that effortless.” — Matt ([105:44])

Takeaway

Matt and Casey make a compelling case for Chicago's status as a gold standard for movie musicals—both as a cinematic triumph and a cultural phenomenon. From its flawless adaptation choices, its transformative casting, and its unique filmic grammar, to its enduring legacy amid a crowded post-2000s field, Chicago is, in Matt’s words, a “no notes” masterpiece. Despite what the "movie bros" or Oscar revisionists say, the film's boldness, musical integrity, and pop-culture traction make its Best Picture win irreproachable.

Diva Send-off:
Casey chooses Bette Midler—“she’s tiny and she’s here” ([114:12])—to play us out.

For more theater geekery, gossip, and deep dives, subscribe to Broadway Breakdown and check out both Matt and Casey’s ongoing projects!