Billy Wilkerson was a true entrepreneur during Hollywood’s Golden Age. He was also a criminal. A native of Tennesee, Wilkerson was in the speakeasy business in New York City during Prohibition. Eventually, he made his way from The Big Apple to Tinseltown.

After founding The Hollywood Reporter in 1930 he turned his attention to nightlife in the City of Angeles by opening several joints around town. The most famous of these was a nightclub called Ciro’s.

James Dean and Ursula Andress

Wilkerson opened Ciro’s in 1940, Wilkerson wanted a place where the stars would come out to play. His thought was that this would help him gain access to celebrities in a more relaxed environment, which would help his trade rag get scoops.

The Ciro’s Scroll signed by 95 stars from 1940 to 1957 including Jack Benny, Lucille Ball, the Ritz Bros., Mary Pickford, Basil Rathbone, Harold Lloyd, Bob Hope, John Payne, Merle Oberon, Jimmy Durante, Roy Rogers, Hoagy Carmichael, Jeanette MacDonald, Joan Bennett, Roy Rogers, Dana Andrew, Claudette Colbert, Harold Lloyd, Ann Miller, Jane Withers, Ross Hunter, Victor Mature, Edgar Bergen, Gloria de Haven, and Yvonne de Carlo.

It was the place to be seen in the 1940s and 50s, smack dab in the middle of the Sunset Strip, a handful of blocks from Beverly Hills. The proximity to the stars was a part of its appeal. So were big-name performers like Peggy Lee, Nat King Cole and Duke Ellington who started to be brought in by the second owner Herman Hoover in 1942.

Marilyn Monroe arriving at Ciro’s in 1954

The interior of Ciro’s was designed by George Vernon Russell and Tom Douglas whose touches and panache were a Christmas-Esque explosion of color and texture, with red silk sofas, ceilings painted a matching red, and walls draped in heavy ribbed silk dyed pale pastel green.

Gary Cooper and Jack Benny at Ciro’s in 1947

One of the features Wilkerson had in this place, where gangsters and starlets rubbed elbows, included a secret room for gambling. He added this at the behest of John “Handsome Johnny” Roselli, a member of the Chicago Syndicate who was a major Mafia figure in Hollywood and Las Vegas. Bugsy Siegel and Mickey Cohen also frequently used this space.

Nancy and Ronald Regan with Jean and Dean Martin in 1952

Before selling it, Wilkerson tried to burn it down for the insurance money. He had previously owned the Trocadero, another club in the 1930s, and had a gangster named Nola Hahn set fire to the kitchen of that establishment back in 1938, so this was the standard operating procedure for Wilkerson.

After Wilkerson sold the club to Hoover to open The Flamingo Hotel in Las Vegas, Mickey Cohen began to extort Hoover out of his clothing shop Michael’s Exclusive Haberdashery at 8804 Sunset. Every week Cohen would send over empty cardboard boxes to Ciro’s in exchange for brown paper bags filled with cold, hard cash.

Nat King Cole performing at Ciro’s in 1954

Fistfights were a common occurrence at Ciro’s. The most famous occurred in 1947 when Frank Sintra was arrested after assaulting columnist Lee Mortimer because the columnist wrote an unfavorable story about Sinatra leaving his wife and children for Lana Turner. Sinatra paid Mortimer $9,000 to get the charges dropped.

A cigarette girl (circa 1940)

Ciro’s permanently closed on May 26, 1956. It marked the end of the era of the Hollywood Nightclub. The location was used as rock venue over the years, first as Le Disc and then as The Kaleidoscope and finally as The Boss. In 1972, it became The Comedy Store.

Kirk Douglas and Rita Hayworth dancing at Ciro’s