Pinky Winters (born Pyllis Wozniak 1 February 1930, Michigan City, Indiana) looms large among the American vocalists of the postwar era. A compelling and nuanced stylist, she nevertheless remains a virtual cipher among the listening public as a result of a prolonged retirement that included a nearly three-decade hiatus from recording.
Born Phyllis Wozniak in Michigan City, IN, on February 1, 1930, she began piano studies at the age of four, she played her first public concert within a year, and throughout her adolescence performed at venues across the northwest Indiana region. Her first influence was Frank Sinatra. As a child she listened to him on the radio. Then she discovered Judy Garland in the movies. She also listened to Dinah Shore and the Andrews Sisters on her father’s wind-up Victrola. One of the first Great American Songbook albums she owned was Ella Sings Gershwin with Ellis Larkins. Naturally, Sarah Vaughan was Winters' major inspiration from the time she was 15.
After graduating from high school, she briefly tenured at an office job before relocating to Denver, gigging alongside pianist Dick Grove where she first used the stage name of Pinky Winters. When Grove and Winters' future husband, bassist Jim Wolf, relocated to Los Angeles in 1953, she soon followed suit, appearing at the Western Avenue club Starlight in a trio with pianist Bud Lavin and drummer Stan Levey. Winters cut her self-titled debut session for the Vantage label in 1954. Like Sarah Vaughan, Winters, had no problem veering away from a song's melody in places. Listening to her find her way back is fascinating. She often took such creative chances on the fly. That's the bold and clever jazz musician in her, the artist who liked to take vocal risks without a net. 
Here's Jeepers Creepers from Lonely One in 1958...
Winters' earliest albums were Pinky (1954), Pinky & Zoot (1954, with Zoot Sims) and Lonely One (1958). During this period, whist married to Wolf, they had a daughter. After releasing the 1958 LP Lonely One, she split from Wolf and got an office job to make
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money to raise her daughter. Eventually she met and married Bob Hardaway, who was on the NBC staff as a saxophone and reeds player. She had another daughter and happily raised her children in their lovely home in the Hollywood Hills. During that time, she didn't sing for 13 years.
money to raise her daughter. Eventually she met and married Bob Hardaway, who was on the NBC staff as a saxophone and reeds player. She had another daughter and happily raised her children in their lovely home in the Hollywood Hills. During that time, she didn't sing for 13 years.In 1980 saxophonist Lanny Morgan convinced Winters to make a comeback appearance at the L.A. club Donte's. Upon divorcing Hardaway later that year, she began working steadily, in 1982 beginning a personal and professional partnership with pianist Lou Levy, a much-acclaimed accompanist who previously worked with Frank Sinatra, Peggy Lee, and Ella Fitzgerald.
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The albums she recorded after returning to performing were The Shadow of Your Smile (1983), Speak Low (1983), Let's Be Buddies (1985), As Long as There's Music (1994), Happy Madness (1994), Rain Sometimes (2001), World on a String (2006) and Winters in Summer (2010).
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The albums she recorded after returning to performing were The Shadow of Your Smile (1983), Speak Low (1983), Let's Be Buddies (1985), As Long as There's Music (1994), Happy Madness (1994), Rain Sometimes (2001), World on a String (2006) and Winters in Summer (2010).
In 1992 she performed with the 52-piece Dutch Radio Orchestra in Hilversum, the Netherlands. Following Levy's 2001 death, Winters teamed with pianist/arranger Sir Richard Rodney Bennett for Rain Sometimes. Since her return to active performing, Pinky has enjoyed stellar recordings and continues to be featured in choice concert settings to the delight of her fans. She has also recorded in Japan , where she toured in 2016.
(Edited mainly from Pinky Winters web site &JazzWax)
An amateur video of jazz singer Pinky Winters at one of her five performances in Tokyo, Japan 12/06. From a late afternoon gig at the intime Cafe Albert, operated in honor of F. Albert Sinatra. Pinky is accompanied by Kiichi Futamura on piano. Two days later, she recorded a live album at the TUC Club.