In 1945 her big-spending boyfriend Irv Hochberg showed Mimi Sheraton a good time her sophomore year at NYU. They went on dates to see Harry James, one of the biggest bandleaders of the day, at the Astor Roof, on Times Square, where crowds had been dining and dancing when the weather was warm since the turn of the century. It had a massive air-conditioned ballroom and a lavishly landscaped outdoor garden where twinkling lights illuminated the promenade at night. The biggest swing bands of the era played there but James was a summer fixture. He broadcast a radio show from the venue. Several of his 1942 broadcasts are available on CD.
Irv also took her to to the Café Rouge at the Hotel Pennsylvania. another major venue for swing bands and radio broadcasts, located across from Penn Station, to see Tommy Dorsey . When she visited him in Yonkers they went to the Glen Island Casino, a restaurant and ballroom in New Rochelle long popular with a younger set. It had an outdoor terrace overlooking the boats on Long Island Sound and Fort Slocum Island and sat on Glen Island Park, which had a bathing beach. According the nightclub reviewer for The New York Times in 1941, the food was "satisfactory." The war was a problem for the venue since most customers arrived by auto and gasoline was severely rationed.
Less to Sheraton's liking was the jazz club Tondelayo's, one of many on West 52nd Street. Irv's cousin Irving Grossberg was playing the saxophone in the house band there. Grossberg, who had a thin beard from his upper lip to his chin and was frequently stoned, was midway in his transformation from Yitroch Grossberg into the famous artist Larry Rivers. Hochberg was writing material for the club's headliner, Tondelayo Levy, and being paid in dinner vouchers. Tondelayo's was not Mimi's style. She remembers it as a “sleazy” joint with bad, overpriced nightclub food. But Irv insisted on ordering the most expensive items on the menu to get his money's worth, likely a tactical mistake in a place like this. You didn't go to West 52nd Street for the lobster. Some of the clubs that lined the street in 1946 were clip joints and dives and drug use was common among patrons and performers. But this was the place to catch the emerging jazz greats who worked outside the hotel ballroom circuit at the time. Among those appearing on the strip the week of April 14 were Art Tatum, Coleman Hawkins and Dizzie Gillespie. Sheraton dismisses Tondelayo Levy as a “slim, dusky and sensuous mulatto...who can do just about anything better than she can sing.” Actually she had been one of the light-skinned stars of the chorus at Harlem's famed Cotton Club, where black entertainers had performed for white socialites and celebrities, and was half of a dance team that had performed at the Club Ubangi. Later in 1946 she was one of the stars of "Sepia Cinderella,' a movie intended for black audiences. Her husband, John Levy, the club's owner, was a well-respected African American bassist, recently arrived in New York from Chicago. He gave Erroll Garner his start in the New York club scene at Tondelayo's and later became the manager of many of the biggest names in jazz.