Roosevelt High School grad 1968

Bob Sirott - A staple of Chicago broadcasting since 1966, (the year he began working as a page for NBC, while in high school) he worked as a page for NBC, Sirott currently anchors the NBC News in Chicago 4:30 broadcast, hosts WGN Radio's Noon Show and co-hosts the WGN Sunday Night Radio Special with his wife Marianne Murciano. Along the way Sirott has alternated between radio and television, working for WBBM Radio, WLS Radio, WTTW TV, Fox TV and CBS Television. In addition to many local Emmys and a national Emmy, Sirott received the Peter Lisagor Award for his reporting on the death of John Lennon

Graduated from Roosevelt High School in 1937. Mr. Gobel (also known by fans as "Lonesome George") was one of the biggest comedy stars of the 1950's. He was best known as the host of his own weekly NBC television show, The George Gobel Show, from 1954 to 1960 for which he won an Emmy in 1954.

Fiorentino was all-city and all-conference in football and captain of the 1976 7-1 Section Champs. Currently, Fiorentino is one of the nations best Mixed Martial Artist and Grapplers. He was nominated for induction into the National Italian American Sports Hall of Fame and in 2008 was the #1 ranked over 40 grappler in the nation. Other accolades include: 1998 Extreme Martial Arts MMA Winner; 2006 NAGA Chicago Grappling Champion Heavyweight Division; 2007 NAGA Midwest Grappling Champion, 2007 Midwest Jiu-Jitsu Champion; 2008 Arnold Grappling Championships, 2008 NAGA Midwest Grappling Championship.

Nelson Algren (1909-1981) - Algren, formerly Nelson Ahlgren Abraham, is a 1928 graduate of Hibbard High School and winner of the 1950 National Book Award for his novel The Man with the Golden Arm. Algren wrote extensively about Chicago's underclass and an annual prize in short fiction is awarded by the Chicago Tribune in his name.

Shel (Sheldon) Silverstein (1930-1999) - Silverstein was an author, poet, and musician. His book of children's poetry A Light in the Attic spent a record 182 weeks on the New York Times Best Seller list. He won a Grammy for his collaboration with Johnny Cash on a Boy Named Sue.