Dinah Washington (August 29, 1924-1963) - Born Ruth Lee Jones, Washington is a towering figure in music and was known as the Queen of the Blues. Washington enjoyed much success during her short career, however, her legacy remains the influence she has had on the legions of artists who have come since.

Eddie Thomas (November 5, 1931-present) - Thomas got his start in the music business as the manager of the Impressions and quickly started his own record label Curtom Records with another CPS alum Curtis Mayfield. From there, Thomas branched into record promotions creating Thomas Associates and worked with many of music's biggest names, Ray Charles, Quincy Jones, and Barry White. He won a Peabody Award for the Rise and Fall of Vee-Jay Records. In addition to music, Thomas is an award-winning poet.

George E. Johnson (June 12, 1927-Present) - In 1971, Johnson Products (make of beauty products) became the first minority owned business to be listed on the American Stock Exchange. Johnson has since dedicated himself to civic leadership, working with organizations like Junior Achievement of Chicago, the Chicago Urban League, the Lyric Opera, Northwestern Memorial Hospital and Operation PUSH. He received Ebony magazine's 1978 American Black Achievement Award, and the 1979 public service award from the Harvard Club for the work of his foundations.

Milton Hinton (June 23, 1910-2000) - Called by some the greatest jazz bassist ever, Hinton was one of the most recorded artists in history. His legacy includes thousands of recordings over the decades with the biggest names in music: Calloway, Gillespie, Goodman, Ellington, Armstrong, Coltrane, Crosby, Streisand, and McCartney. In addition to his music, Hinton is also remembered for his photographs. In his lifetime, he took over 60,000 photographs of the biggest musicians at various stages in their careers.

Nat King Cole (March 17, 1919-1965) - Born Nathaniel Adams Coles, Cole was a popular singer, songwriter, pianist, and performer. He recorded 28 Gold Records and became the first African-American to host his own television show. He was inducted into the Rock and Roll Hall of Fame in 2000.

Born Sam Cook, he added an "e' to his name and became Same Cooke. (January 22, 1931-1964) - Sam Cooke was a charter member of the Rock and Roll Hall of Fame. His first single, You Send Me, spent six weeks at number one. He once sang in a group with another CPS alumnus, Lou Rawls.

Sunder Lamont Nix (December 2, 1961 – Present), a 1984 Olympic Gold Medalist for men’s 4x400 meter relay race, earned a degree in Criminal Justice at Indiana University and is currently Assistant Coach of men’s track and field for Ball State University.

Sylvester Monroe ( August 5, 1951 – Present) – Monroe started his journalism career with Newsweek serving in Boston and Chicago before landing at Newsweek's Washington bureau. His acclaimed reports include "Why Johnny Can't Write", "American Innovation", and the three part series "Why Public Schools are Flunking".
His story on seven friends from Chicago’s housing projects was turned into a best selling book: Brothers: Black and Poor—A True Story of Courage and Survival. In 1989, Monroe joined Time’s L.A. Bureau and in 2001 became the Atlanta Journal – Constitution’s Sunday editor for the National /Foreign Desk. Currently, Monroe is the senior editor of Ebony Magazine and much sought after speaker.

Harlem Globetrotters (1926-present) - Originally called the Savoy 5, the Harlem Globetrotters were assembled in 1926 and comprised mostly of players from Wendell Phillips High School. In all, 13 players from Phillips would play for the Globetrotters over the years: Tommy Brookings, Hillary Brown, George Easter, William "Razor" Frazier, Roosevelt Hudson, Inman "Big Jack" Jackson, Lester Johnson, Byron "Fat" Long, William "Kid" Oliver, Al "Runt" Pullins, Randolph Ramsey, Ted Strong, Walter "Toots" Wright