United States of Kennedy – “Film of the Month: Bobby (2006)”

Podcast: United States of Kennedy
Hosts: George Civeris, Julia Claire (guest, comedian/writer at Crooked Media)
Episode Date: October 27, 2025
Episode Focus: A critical, lively review of Emilio Estevez’s 2006 film Bobby, examining its take on Robert F. Kennedy (RFK), its all-star ensemble, and its place in Kennedy pop culture.

Overview

This episode explores the 2006 film Bobby, written and directed by Emilio Estevez, which dramatizes the day RFK was assassinated at the Ambassador Hotel through the eyes of various fictionalized characters. Hosts George and guest Julia discuss the movie’s approach to history, its massive cast, its emotional ambitions, and where it falters (and occasionally succeeds) as a tribute to RFK and the turbulent era of the late 1960s.

Key Discussion Points & Insights

1. Kennedy Fascination: Personal and Cultural

• Julia shares her longstanding obsession with the Kennedys, especially Bobby, having read Larry Tye’s Bobby Kennedy biography years ago (05:05).
  • “I think there's a Massachusetts specific fascination with the Kennedys that's not entirely healthy.” – Julia (05:31)
• Both agree Bobby and Ted are more interesting than JFK, highlighting Bobby’s emotional complexity and Ted’s longevity in public life (06:32, 07:05).

2. RFK: Legacy and Contradictions

• Bobby is portrayed as the 'emotional' Kennedy – complex, temperamental, with a “notoriously terrible temper … a little teapot waiting to blow.” – Julia (06:32)
• The film’s hagiographic tone is critiqued:
  • “It is a classic ensemble movie that doesn’t quite add up to more than the sum of its parts.” – George (02:46)
  • Both hosts point out that RFK’s record on civil rights (including his connection to Joseph McCarthy and MLK wiretaps) is glossed over (08:34).
• Famous scene recounted: Bobby’s contentious meeting with civil rights leaders organized by James Baldwin, in which RFK seeks validation but instead is told he hasn’t done enough (10:48). “He was pissed at the time. He wanted to be celebrated for being a civil rights champion.” – Julia (11:13)

3. How the Film Was Made (Casting & Sentiment)

• Anthony Hopkins was first to sign on, sparking a “domino effect” among A-listers—all reportedly worked for scale due to their passion for the project (20:51–22:38).
  • “...all these big actors basically just had five lines. I am sure that for Sharon Stone it was one day on set.” – George (22:46)
• Not much critical bite: “A movie like this, it would be very easy to pretend you’re being a little more objective... but every single storyline, it’s like the arc of the universe bends towards Bobby Kennedy being the perfect American.” – George (12:40)

4. Ensemble Structure: Successes and Pitfalls

• Hosts attempt to catalog the sprawling cast and their interconnected, synecdoche-like stories (15:44–17:45). Notably:
  • Anthony Hopkins and Harry Belafonte as wise old friends in the hotel.
  • Lindsay Lohan marries Elijah Wood’s character to keep him out of Vietnam; inspired by a real incident (16:01).
  • Sharon Stone as salon worker, William H. Macy as hotel manager, Demi Moore as an alcoholic singer, and so on.
• The film’s structure is likened to Robert Altman’s Nashville, but, “It’s like the Altman ensemble thing, except none of the stories really connect in a satisfying way.” – Julia (17:45)
• Sharon Stone’s character is unique in not being a direct symbol of a 1960s “social issue,” making her the most believable (27:32).

5. Best and Worst Performances

• MVPs: Anthony Hopkins, Laurence Fishburne, and Sharon Stone—“It’s basically like they’re acting in a different movie.” – Julia (23:26)
• Memorable/Laughable: Helen Hunt’s “black shoe monologue” about the injustice of mismatched shoes for rich women is lampooned for its shallow feminism (24:07).
• Nick Cannon’s performance is flagged as “the most unforgivable overacting in the whole movie” (34:51), notably saddled with lines like “Now that Dr. King is dead, Bobby is all we have” (09:48, 35:03).

6. Critique of Direction and Screenplay

• The film is seen as “a labor of love” but uneven—George calls it a “tepid flop” (48:02).
• Repeated theme: Estevez’s heartfelt but clumsy approach—“Honey, he should have had a team.” – Julia (12:18)
• Some moments are genuinely moving, mainly due to powerful archival footage and music rather than the fictionalized drama.
  • “...the last five minutes of it, I’m getting a lump in my throat. And that’s crazy.” – Julia (30:03)
• The film tries to address every social issue at once, resulting in shallow segments and underdeveloped characters—“The film sacrifices depth for breadth.” – George (31:21)

7. Iconic/Cringeworthy Moments

• LSD Acid Trip Sequence (32:08–33:21): A bizarre, over-stylized detour with Shia LaBeouf and Ashton Kutcher, featuring green-screen hallucinations, described as “a crazy thing to put in the middle of this movie.”
• Demi Moore’s Cabaret Performance: Her “Louie Louie” cover and grand hair become running gags.
  • “She’s like, I’m here to slay. Like, I came here to play a drunk cabaret singer, and I do not even know who y’all are voting for.” – George (44:35)
• Sharon Stone’s nail salon scene is cited for authentic emotional resonance; Demi Moore’s meltdown—“We’re all whores. Some of us are just paid for it.” – Demi Moore as Virginia Fallon (27:06, 44:36).

8. Historical Accuracy and RFK Portrayal

• Strong praise for NOT casting an actor as RFK—his presence is brought in entirely via archival footage (38:38):
  • “I really liked that....when he is shot, and then there is a scene being filmed around him, it seamlessly switches into archival footage.” – George (38:58)
• Julia believes the film fairly reflects RFK’s effect on those who loved him: “He really touched people. He was so emotional himself....Everything for him was visceral and tactile.” – Julia (41:22)

9. Final Takes and Lingering Questions

• The ambiguous fate of several characters post-shooting is noted, with the ending making it unclear who lived or died. Only the final title card clarifies this (49:19).
• The film is ultimately labeled “pretty boring, honestly” and emblematic of a missed opportunity, but not without fleeting power thanks to real footage and music (“The Sound of Silence” montage gets a mention for inducing chills, 29:12).

Notable Quotes & Moments (w/ Timestamps)

• “I cracked open my Bobby Kennedy biography for the first time in years.” – Julia (05:05)
• “It almost feels like famous Oscar-nominated actors were walking by the set and the director was like, do you want to just come in for one scene?” – George (04:54)
• “He was not as naturally smart as Jack. Definitely not as naturally charismatic.” – Julia (07:51)
• “He completely fucked that up as well after, like, years of trying to make it his signature, number one thing. But I think maybe the propaganda of this movie partly worked on me.” – George (08:01)
• “The hagiographic tone of the movie really cannot be overstated.” – George (11:46)
• “If this movie had 30% more her [Sharon Stone]...it would have been a lot better.” – Julia (27:55)
• “The last five minutes of it, I’m getting a lump in my throat. And that’s crazy.” – Julia (30:03)
• “He died as just a symbol of hope and change. To quote a different politician.” – George (42:45)

Segment Timestamps

• 02:46 — Summary of Bobby’s history, assassination context, and the film’s premise
• 05:05–07:05 — Julia’s personal Kennedy & RFK fascination
• 08:34–11:13 — Civil rights, Bobby’s controversial legacy, Belafonte/Baldwin meeting
• 12:07–13:22 — Emilio Estevez’s Kennedy connection, making of Bobby
• 15:44–17:45 — Rundown of ensemble cast and characters
• 20:51–22:38 — How Anthony Hopkins recruited the cast, film as “passion project”
• 23:26–24:07 — MVP actors and the infamous “black shoe monologue”
• 27:06–27:32 — Standout Sharon Stone, archetypal vs. real characters
• 29:12–30:11 — Montage, archival footage, and emotional payoff
• 31:21–32:47 — LSD sequence, film’s lack of focus
• 38:38–39:54 — Praise for only using archival Bobby footage
• 41:22–43:27 — How well the film captures the real Bobby’s charisma/legacy
• 44:35–46:21 — Demi Moore’s performance; “We’re all whores” scene
• 47:21–47:39 — Sharon Stone’s improv haircut of W.H. Macy
• 48:01–48:49 — Film as “tepid flop,” Lindsay Lohan as “our Bobby Kennedy”
• 49:19–50:08 — End confusion: who died, who lived

Conclusion

Despite a sincere, even loving attempt at broad historical resonance and an all-star cast, Bobby misfires as both drama and history lesson, saved only momentarily by its real archival material and the odd actor who seems to be in another, better film. The discussion is equal parts affectionate lampoon and wistful “what could have been”—reflecting a cultural Kennedy obsession that, like the subject’s legacy, refuses to die.