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William Shatner

Captain James T. Kirk

Leonard Nimoy

Mr. Spock

DeForest Kelley

Dr. McCoy

Anthony Caruso

Bela

Vic Tayback

Krako
(as Victor Tayback)

Lee Delano

Kalo

James Doohan

Scott

Nichelle Nichols

Uhura

Walter Koenig

Chekov

John Harmon

Tepo

Sheldon Collins

Tough Kid

Dyanne Thorne

First Girl

Sharyn Hillyer

Second Girl

Buddy Garion

Hood

Steven Marlo

Zabo
(as Steve Marlo)

Benjie Bancroft

Iotian Passerby
(uncredited)

Bill Blackburn

Lieutenant Hadley
(uncredited)

John Blower

Crewman Swenson
(uncredited)

Did you know

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Trivia
After filming wrapped the studio received a letter from Anthony Caruso, who played Bela Oxmyx. It was a letter from "Oxmyx" thanking the crew of the Enterprise for creating the "syndicate" and things were proceeding nicely on Sigma Iotia II. As he goes on in the letter, it is now the 1950s and he is sporting a crew-cut. He also mentioned wanting to visit Las Vegas, remarking "It seems like my kind of town."

Goofs
The two thugs are killed in the opening segment are wearing the same suits worn later by two other thugs who are made to give their clothes to Kirk and Spock.

Quotes
Spock: [Gangster accent] I would advise yas to keep dialin', Oxmyx.

Alternate versions
Special Enhanced version Digitally Remastered with new exterior shots and remade opening theme song

Connections
Featured in William Shatner's Star Trek Memories (1995)

Soundtracks
Theme
Music credited to Alexander Courage
Sung by Loulie Jean Norman

Hilarious, Tongue-In-Cheek Episode

In what must be one of the funniest episodes of the series (and a great indicator of the series' intentional comedic possibilities -- brought to fruition in Star Trek IV: The Voyage Home), the Enterprise crew visits a planet that has taken a historical text on 1920s Chicago gangs as its bible. As the residents of the planet are remarkably imitative in nature, the planet's residents have divided themselves into a series of criminal gangs, two of which are headed by Bela Oxmyx (Anthony Caruso) and Jojo Kracko (Vic Tayback), and Kirk and Spock find themselves in the middle.

What makes this otherwise frivolous episode work is the fun Shatner and Nimoy have with the historical disconnect -- most notably in Kirk's efforts to drive a car (and Spock's reactions thereto) and his subsequent efforts to pick up the lingo of the planet. Needless to say, Shatner plays this for all it's worth, and Nimoy's gift for understatement complements it beautifully.

Truly a joy to watch -- just don't spend too much time analyzing it.