Life on the road for the big bands was difficult at the best of times, but for the integrated bands travel, particularly in the South with the "Jim Crow" laws, could be overwhelmingly cruel. Black members were rarely permitted to stay in the same hotels or eat in the same restaurants as the white members.
One story concerns Frank Sinatra during his Dorsey years in the early 40's, and the band's arranger Sy Oliver, who was black. While the band was checking into a hotel, the clerk dispensed room keys to Sinatra and the other white members, but froze when he spotted the black arranger in the group.
He refused to give him a key and indicated that he was not welcome in the hotel. Francis Albert Sinatra, no stranger to ethnic discrimination from his days in Hoboken, New Jersey, reportedly reached across the counter, grabbed the clerk by the tie, pulled him across the counter and simply said, "He stays". Sy Oliver stayed.
Sy Oliver was the arranger for Dorsey's great recording of "On The Sunny Side of The Street"
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