Howard A. Olson

The Great Chesterfield, signed publicity photograph from his Chicago vaudeville years. Photo: Ventriloquist Central

Howard Axel Olson wasn't supposed to go into show business. His family was Swedish and hardworking, and show business wasn't a thing they approved of, so around the time he started performing he picked a name that would keep the peace at home: The Great Chesterfield.^[1] He kept his own name off the marquee for most of a long career, which is probably part of why history remembers his son's face better than his. This is the man who was already doing Chicago vaudeville before that son could talk, the one who started the whole family trade in the first place. Pull up a chair. Let me tell you about the original Olson.

A cutting room, and a shop on Clarke Street

He taught himself ventriloquism on the job, working days at a Chicago silk wholesale house.^[1] He had charge of about fifteen young stock boys down in the cutting room, and when the road salesmen came through the door full of pep, he started throwing his voice to imitate the house usher, calling the salesmen by name as if a customer had arrived. They'd hustle out to the salesroom and find nobody there.^[2] One of his own stock boys told him he was as good as a ventriloquist he'd seen work an actual stage, and took him to see for himself: a Chicago furniture and wood-carving shop on Clarke Street run by the Mack brothers, Theo and Charlie.^[2] In 1911, Howard bought his first figure there, a red-wigged boy with a name that would outlive him by eighty years: Reddy.^[1] The price was eleven dollars.^[1]

Ten minutes on State Street

His first date was a small show on State Street, and it lasted ten minutes before the owner, a man who later ran some of Chicago's biggest movie houses, delivered the verdict flat: "You're a ventriloquist all right, but you haven't got a thing."^[2] Chesterfield's own moral, retold years afterward: so you see, even with a Mack figure, you couldn't get by without good material.^[2] He went six months after that without seeing another ventriloquist work, with no real idea what material even looked like.^[2] He found it eventually, the same way most of this trade eventually does: by studying somebody better. Whenever the Great Lester played Chicago's Majestic Theater, Chesterfield was in the seats, learning from the master.^[1]

Chesterfield and Little LeRoy

By the time his own son was seven years old, Howard had built a full double act around him, billing the pair as "Chesterfield and Little LeRoy."^[1] That boy grew into a nearly sixty-year career of his own, first as Little LeRoy, then as Chester LeRoy, and by 1957 simply as Howie Olson, the man who spent eleven years hosting live children's television in Madison, Wisconsin with a figure named Cowboy Eddie.^[5][6] Cowboy Eddie, as it turns out, was Reddy: the same eleven-dollar figure Howard bought on Clarke Street in 1911, renamed and carried through fifty more years of stages and television cameras by the boy he'd trained.^[7]

Father and son shared a profession, a first name, and eventually a figure. They didn't share a stage name, an act, or a set of dates, and this trade has had to work to keep the two of them straight in its own records.^[3][4] Keep them straight and the story only gets better: it isn't one man's career. It's a family's, run in relay. In May 1952 the Oracle, the newsletter of the International Brotherhood of Ventriloquists, put it in print exactly that way, describing the son working Houston as "the son of Howard A. Olson, of Chicago, professionally known as The Great Chesterfield."^[8]

The Oracle years, and a bell in the woods

The Oracle kept tabs on Chesterfield well into his seventies. In June 1954, at around seventy-two, he performed his old vaudeville act at the IBV convention in Louisville, Kentucky, one of twenty acts on the bill.^[9] He was still working Chicago the following summer.^[10] By 1956 he was performing with a figure built by Frank Marshall, the Chicago maker whose bench turned out figures for Edgar Bergen, Paul Winchell, and a long list of the era's touring vents.^[11]

Then in 1957 he sent the Oracle something better than a review. It was a Chicago Daily News Roto Section photograph of himself, sixty-five years old at the time, standing on the ground that had since become Wrigley Field, back when it was still a hilly stretch of woods.^[12] Run the math on that and the picture puts him there around 1892, a boy of about ten, years before anybody thought to put up a ballpark. Later that same year he missed the Houston convention because his son Bob had been hospitalized, the only mention this record keeps of a second son besides the one who went on to build Cowboy Eddie's long career.^[12]

Jake, and the girl who remembered him

By the 1950s his own figure had a new name too: Jake.^[3] One day, carrying Jake in a suitcase, Chesterfield got waylaid by thieves looking for something worth stealing. They popped the case, found nothing but a small wooden boy, decided he had no value, and left him right where he was.^[3] Chesterfield liked that story well enough to keep telling it, and it outlived him.

Decades later his own granddaughter, Karin Grace Olson, wrote in to a ventriloquism newsletter to say she'd been raised by "Gramps" in Chicago after her parents separated in the mid-1950s, and that she remembered him out and about with Jake exactly the way the old story described.^[13] She placed her uncle Chester LeRoy in Madison, Wisconsin, tied to a television character called Cowboy Eddie, though she was honest that she wasn't sure of the years.^[13] Howard Axel Olson, The Great Chesterfield, died in Chicago on February 26, 1977, ninety-four years old.^[1][13]

Every figure in this trade traces back to somebody's first bet on themselves. His was eleven dollars, made in 1911 in a Chicago wood shop, and it kept working for fifty more years in someone else's hands, long after the woods he used to ring a bell in had grown over into a ballpark.

Eleven bucks for Reddy, and the house manager still said he had nothing. Sixty-six years of paychecks later, I'd call that the best bad review in the business.— Freddy Fiddlesticks, spokesdummy