The Gangster That Gangsters Loved

Sheldon Leonard looked like a gangster. Sheldon Leonard sounded like a gangster. Guess what parts Sheldon Leonard played?

Well, yes, he did more than underworld and shady characters; he was even a cartoon lion for a while. But Leonard was smart. He knew supporting roles like that wouldn’t lead to huge amounts of fame or fortune so, instead, he turned to television producing. He turned out to be one of the most intuitive producers of the late ‘50s and early ‘60s.

The odd thing is that real gangsters loved his romanticised portrayal. Here’s a story from early 1952. There’s also a mention of my favourite role of Leonard’s where a few times every season, he’d appear on Jack Benny’s radio show and give confidential racing-form type tips on the best elevator, restaurant table, sleepwear—everything except horses (“Who knows about horses?” he asked Benny on one show set at a race track).

Film Gangster Is A Hero To Some Fans
By GENE HANDSAKER
Associated Press Staff Writer
Hollywood, Jan. 8. —Sheldon Leonard isn't a gangster, has never been one, and doesn't intend ever to be one. But judging from roundabout compliments he has received, he's a sort of hero to shady characters in real life.
"I play 'em the way they figure themselves to be," Leonard explained the other day. "Omnipotent — with a cold detachment."
You probably have heard him as that hollow-voiced race-track tout on the Jack Benny radio program. His unchanging opening line—"Hey, bud ... Where ya goin'?"—never fails to get a big laugh. For this reason, Sheldon calls it "the most rewarding role in show business for the amount of energy expended."
He's also a reformed counterfeiter on Phil Harris' program, the boy friend on Judy Canova's show, and a hobo on a broadcast called "It's always Sunday."
Has Two Children
He has played assorted gangsters in about 35 movies and is used to being told: "I'll never forget the way you kicked Alan Ladd in the head in 'Lucky Jordan' . . . and the way you slapped Lauren Bacall in 'To Have and Have Not.' "
The real-life Leonard is dark-complexioned, with brown eyes, wavy hair, and, a worldly savoir-faire usually associated with gangster roles.
The father of two, he is a respectable member of the Parent-Teacher Association, whose other members frequently compliment him on his outlaw portrayals. A graduate of Syracuse University, where he majored in speech, Leonard tosses around shrewd observations on gangster portrayals.
"We tend to satisfy masochistic urge in certain women. We're all merchants, and I'll sell whatever is commercial. But I've skimmed the cream off the heavy type of thing. There's a more rewarding market, I believe, for the Bill Bendix type thing from now on— the likable mugs."
In a picture called "Decision" he plays a sympathetic character for the first time. He's devoted to a hunchback brother and wins the love of Anne Gwynne. Yes, Sheldon says he's tired of playing gangsters.
"This fishy, glacial exterior isn't acting. You just sit there and let your complexion and eyeballs sell the character."

Leonard never gave up appearing on camera altogether. In fact, he starred in Big Eddie, a show with a fine cast but survived only ten episodes before being cancelled in 1975. But it was as a producer of The Dick Van Dyke Show, I Spy and other shows where he made his mark—besides being the gangsters’ pin-up boy.