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Red Holloway's storied career had auspicious beginnings. While playing in DuSable High School's big band in Chicago in the mid-1940s, Holloway and fellow saxophonist Johnny Griffin were sometimes visited by jazz royalty, such as Duke Ellington, Lionel Hampton and others, who would stop by the school and sit in with the band. Holloway says that's where Hampton discovered Griffin and where he was recruited by bassist Gene Wright (who would later join Dave Brubeck's quartet).
"Most of the fellas in his big band were playing with Dizzy Gillespie," Holloway remembers. "We used to win all the big-band contests."
Holloway spent the next three years in Wright's band before heading to the Army for almost a year. When he returned to Chicago, he spent a lot of time at a club above the city's famed Grand Terrace ballroom, where Louis Armstrong once played. "We had a musicians' club, where, when musicians came to town and they didn't have anywhere to stay, they could stay at this club," Holloway explains. "They had jam sessions all night long. I met Dexter Gordon, Yusef Lateef and Sonny Stitt there."
Stitt and Holloway formed a friendship at the club and ended up touring together. Stitt is the one who encouraged him to switch from tenor to alto sax. "He saw that I had an alto and said, 'Bring that out on the road with you,'" Holloway recalls. "'Are you crazy?' I said. 'I'm catching hell just playing tenor with you.' He said, 'Yeah, but people wanna see you cut me.' I said, 'Yeah, with a knife — but not playing this alto.' But anyway, I started playing alto, and I've been playing ever since. There were a lot of cutting sessions on the road, but, of course, he was the champion, no question about that."
Considering the company Holloway's kept over the years — he's performed with Billie Holiday, Clark Terry, Harry "Sweets" Edison, Eddie "Cleanhead" Vinson and blues legends Etta James, Roosevelt Sykes, Willie Dixon and Muddy Waters — that's a high compliment. But while he's played his share of jazz gigs, Holloway says the blues gigs were the ones that helped him support his wife and child and ultimately helped make him a more versatile saxophonist. ("When [harmonica player] Little Walter started playing with Muddy," Holloway notes, "that was the end of the saxophone.") As a result, today he's equally at home growling on funky, greasy barrelhouse blues and swinging heavy on jazz standards.