'Wall Street'
The Ringer's Bill Simmons takes a young stockbroker named Brian Koppelman under his wing to teach him the tricks of the trade. We take the subway to downtown Manhattan to revisit the 1987 Oliver Stone film 'Wall Street,' starring Charlie Sheen, Michael Douglas, and Martin Sheen.

Cast
Michael Douglas as Gordon Gekko
Charlie Sheen as Bud Fox
Daryl Hannah as Darian
Martin Sheen as Carl Fox
Terence Stamp as Sir Larry Wildman
James Spader as Roger Barnes
Hal Holbrook as Lou Mannheim
John C. McGinley as Marv
Sean Young as Mrs. Gekko
Directed by: Oliver Stone
Written by: Oliver Stone, Stanley Weiser
Notes
- Budget $16.5 million; grossed $41 million.
- Michael Douglas was the fourth choice for Gekko – after Warren Beatty, Richard Gere, and Al Pacino.
- Tom Cruise wanted the Bud Fox part but Stone was committed to Charlie Sheen; they later worked together on Born on the Fourth of July.
- The 'Greed is Good' line was based on Ivan Boesky's real speech to the 1986 Berkeley business school graduating class.
- Stone filmed on the actual NYSE trading floor (45 minutes with real brokers) – no film had done this before.
- Shot in 53 days, came in 7 days early and ~$2 million under budget due to an impending directors' strike.
- Douglas was smoking 40 cigarettes a day and had to work with a speech instructor on breath control for the rapid-fire dialogue.
- Charlie Sheen was only 22 during filming; hung out with real young brokers at Bear Stearns and Salomon Brothers to prepare.
- Pat Riley connection: Douglas and Riley were friends; Riley's slicked-back hair look was mutual inspiration with Gekko's look.
- Stone went to Douglas's trailer early in filming and challenged him – both have competing versions of this story to this day.
- Sean Young tried to steal Daryl Hannah's part mid-filming, confronting Stone in front of Hannah.
- Hal Holbrook's character modeled on Stone's father, who was on 'Wall Street' for ~30 years.
- Brian Koppelman says 'Wall Street' is one of 5-6 things that most influenced Billions and 'Rounders'.
Categories
Quote from Rog's review:
“The movie has a traditional plot structure: The hungry kid is impressed by the successful older man, seduced by him, betrayed by him, and then repents.”
- Bud Fox's first meeting with Gekko – the 5-minute office scene, 'you're the kid who called me 59 days in a row' (Koppelman's pick).
- Martin Sheen/Gekko meeting with union reps + the elevator fight – 'he came into Egypt, a pharaoh who did not know' (Bill's initial pick).
- Gekko's limo pep talk – 'you could be a player or nothing'.
- The 'Greed is Good' Teldar speech.
- Bud buys the apartment / Talking Heads montage – wine, pasta, sushi, smoking jacket.
- The final Bud/Gekko confrontation with the wire – 'I gave you your manhood, I gave you everything'.
- Terence Stamp as Sir Larry Wildman – so modern and classic (Koppelman's pick).
- Real-life family members playing family (Martin & Charlie Sheen) (Bill's pick).
- James Spader playing the same role he'd play 27 more times.
- Sushi used as an exotic foreign device – now its own economy.
- Various quotable lines – 'man looks in the abyss,' 'money never sleeps, pal'.
- One of the first private jet scenes in a movie.
- Cigarette smoking everywhere.
- Daryl Hannah's performance and character – miscast, bad writing for the part; Stone's quote about making her cry on set wouldn't fly in 2020.
- Gekko's gigantic cell phone and handheld TV with two-inch screen.
- Blue Star's lead union rep – bad actor, 'out of a Laverne and Shirley episode'.
- The 'Wall Street' sequel (Money Never Sleeps).
- Darian's plan to 'do for furniture what Laura Ashley did for interior fabrics'.
- Michael Douglas was the fourth choice – after Warren Beatty, Richard Gere, and Al Pacino.
- Tom Cruise wanted Bud Fox but Stone was committed to Charlie Sheen.
- Jack Lemmon was offered as an alternative to Martin Sheen for the father; Charlie picked his real father.
- Charlie Sheen in the Bud/Darian breakup scene – 'he's on Def Con 11' (co-winner).
- Sylvia Miles as the real estate broker – 'Of course, I'm taken, honey' (co-winner).
Franklin Cover (from The Jeffersons) (winner).
- Terence Stamp – only two scenes (Gekko's office and the yacht), completely steals them (winner). 'Eight minutes, four threes'.
- Sean Young – two scenes, 'throwing 140 miles an hour'.
- John C. McGinley – nothing part but stands out.
- James Karen – Sheen's boss, the confused 'no, no, you're welcome' moment.
- Michelle Pfeiffer for Darian (Bill's pick).
- Melanie Griffith for Darian – 'Working Girl' era (Koppelman's pick).
- Diane Lane for Darian – both agreed she would have been great.
- Robert Duvall as the father if Tom Cruise had been cast as Bud Fox.
- Michael Douglas: Yes – this plus 'Fatal Attraction' makes him the biggest male star in the world.
- Oliver Stone: This era – Platoon then 'Wall Street' back-to-back.
- Charlie Sheen: As an actor, this or Platoon; as a celebrity, Two and a Half Men.
- Squash: Koppelman picks this as an apex.
- Steak tartare: Koppelman says this is the high point.
- The Hamptons: Early/stealth Hamptons, before it became widely known.
- Was Bud really dumb enough to think Gekko wasn't going to destroy Blue Star?
- Gekko wouldn't have worried about Bud wearing a wire – he was too smart not to check.
- Gekko didn't say enough in the wire scene to actually get arrested.
- One of the worst dubs ever during Gekko's speech – 'This is an outrage, you're out of line, Gekko'.
- Bud becoming a dick to his best friend Marv way too quickly.
- No Emilio Estevez cameo (could have played a union rep or another Fox son).
- The giant cell phone from the Hamptons sunrise scene (Bill's #1 pick).
- Sir Larry's walking stick/cane (Koppelman's pick).
- The automatic sushi machine (Koppelman's friend actually bought one off eBay for $300).
- The blue skeleton-head painting in Bud's apartment (a Julian Schnabel, now worth ~$70 million).
- Did Charlie Sheen eventually just turn into Bud Fox? (Answer: Yes).
- How much did Gordon Gekko lead to Trump's late-80s billionaire persona? (Bill says about 10%).
- If you switch Cruise and Sheen between 'Cocktail' and 'Wall Street', are both movies worse, better, or what?
Already essentially happened with Billions on Showtime.
- Michael Douglas – the movie plus 'Fatal Attraction' made him the biggest star in the world; he forever owns one of the most important characters in cinema history.
- Bill also makes a strong case for Oliver Stone (Platoon + 'Wall Street' back-to-back) but ultimately goes with Douglas.