The close friendship between Lee and Sinatra began when they both played at the Paramount Theater in New York in 1941, and it would continue until his death in 1998. “There have been very few men in our business,” wrote Lee, “who have effected me so deeply...” About Lee, Sinatra said, “Her wonderful talent should be studied by all vocalists; her regal presence is pure elegance and charm.”

Lee and Sinatra both began as big-band singers (she with Benny Goodman, he with Tommy Dorsey). While they were both still in their 20s, they each shifted to solo careers. Both Lee and Sinatra signed with Capitol Records, and through the 1940s and into the 1950s each of them worked with the best arrangers — including Gordon Jenkins, Nelson Riddle, and Billy May. Lee left Capitol for Decca Records in 1952 (over a dispute concerning her idea to radically remake the Richard Rodgers’ song “Lover”). When Lee’s Decca Records contract expired in 1957, Frank Sinatra told the head of Capitol Records to “get Peggy back.”

Their similarities of approach are evident throughout 1957’s The Man I Love — Lee’s first album after her return to Capitol. It was an outstanding album of ballads conducted by Sinatra and arranged by Riddle. (Sinatra received equal billing with Lee on the album’s cover). Sinatra was at his best when singing about the dark and desperate side of love, as evidenced on his own 1950s Capitol Records masterpieces In the Wee Small Hours and For Only the Lonely, and here Sinatra brought Lee into his ideas of creating a conceptual album. Lee preferred warm, optimistic ballads, and she was not a confessional singer in Sinatra’s sense. Supported by Sinatra’s deep personal involvement and sensitive conducting, and Nelson Riddle’s sweeping orchestrations, Lee sings with an openness and depth of feeling that is just as characteristic as the sensuality she put across in her hits “Black Coffee” and “Fever.”

Of course, Peggy Lee and Frank Sinatra each enjoyed long influential careers into the 1990s. In 1957, The Man I Love was a landmark creative meeting point for these two musical giants.

This Tribute to Peggy Lee and Frank Sinatra celebrates two musical icons who were not simply labelmates, but best friends and close creative colleagues. Our fantastic guest artists — Billie Eilish, Debbie Harry, Dianne Reeves, Bettye LaVette, Seth MacFarlane, Brian Stokes Mitchell, Gretchen Parlato, John Beasley, and Carmen Bradford, performing with music director Christian McBride and the Count Basie Orchestra led by Scotty Barnhart — bring their own distinctive interpretive brilliance to songs from the Peggy Lee and Frank Sinatra catalogs. We hope everyone attending this special concert event at the Hollywood Bowl will feel as delightfully inspired as everyone involved in this production.

Thank you and enjoy!

—Danny Kapilian