A native of Chicago and now a resident of Las Vegas, Nevada,
Diana has enjoyed a wide variety of musical endeavors. While in high school she was a member of various choral ensembles, a featured artist in annual talent shows and for all 4 years of high school, was a member of Chicago’s All-City High School Chorus with her final performance at Chicago’s Orchestra Hall. She studied voice at Kennedy-King College and earned her associate in arts degree in Liberal Arts.
For decades, Diana has lent her powerful, fiery vocal stylings and choreography to some of the biggest names in classic Blues, Soul and R&B. Her most notable musical associations include:
Otis Clay, spending several years touring the world and recording as one of the core backup vocalists for the Blues Hall of Fame inductee, performing alongside fellow veteran singers Theresa Davis formerly of the Emotions and Diane Madison, formerly background vocalist for Aretha Franklin.
The Lost Generation: She worked with The Lost Generation who had their big 70’s hit “The Sly, the Slick and Wicked” and after the groups reforming with her husband Fred Simon, the last original member, Charles Jackson and Audra Rushing scored another hit single entitled “Thinkin’ Bout Cha” in 2003.
The Chi-Lites: She regularly performs and tours with the iconic legendary 70’s soul group, contributing her versatile vocal styling to their live performances.
And has performed with Melvin M. Miller, Recording Artist, Composer, Educator and Radio Personality; Michael Logan, Composer, Arranger, Writer and Performer; Steve Keys, brother of gospel artist John P. Keys; Jack Krammer and his Orchestra and High Society.
While Diana is celebrated as an anchor for major soul ensembles, she is stepping out front as a solo artist and is now continuing to work on her music projects.
Personal Life
Diana Simon is the widow of the late R&B legend Fred E. Simon III, a co-founder and member of the prominent Chicago vocal group The Lost Generation and vocal group Mystique, before his passing a touring member of The Chi-Lites. Following his passing March 29, 2026, she is continuing to contribute as a vital figure in the preservation of classic soul and R&B.
