Chicago is one of the great music capitals of the world, so it should come as no surprise that CPS alumni are among the most important and influential musicians of the last century.
To celebrate the accomplishments of our former students, CPSalumni.org has created an iMix on iTunes comprised entirely of our alumni's work for you to enjoy. Click here to view the playlist on iTunes. Otherwise, playlist is copied below. Also be sure to check out the conversation about this list on District299.com.
Most of the musicians listed below were tracked down to CPS via the graduation records (1873-1973) available through CPSalumni.org. If you attended or worked for the Chicago Public Schools, or have family who did, we invite you to register for free now.
With too many chart topping songs to choose from, this is only a humble sample of the some the great musicians and music from CPS alumni. Many of the best sidemen, studio, and touring musicians for hire in the business are also CPS alumni. Other popular musicians like Rhymefest, and DaBrat also attended CPS schools; unfortunately, their lyrics were too strong for inclusion here. Also, we are certain Grammy winner Lupe Fiasco attended CPS, but don't know what school(s). If you know, please email editor@cpsalumni.org. Thanks.
| Song | Artists | Genre | CPS School's Attended |
| Nobody's Sweetheart | McKenzie and Condon's Chicagoans (4 members of the Austin High Gang) | Jazz | Austin High School |
| Soul Bossa Nova | Quincy Jones | Jazz | Raymond Elementary |
| Sing, Sing, Sing (Remastered 2001) | Benny Goodman & Benny Goodman & His Orchestra | Jazz | Shepard Elementary Harrison High School |
| Comin' Home Baby | Mel Tormé | Jazz | Shakespeare School Hyde Park High School |
| Relax Max (Single) | Dinah Washington | Vocal | DuSable High School |
| Unforgettable | Nat "King" Cole | Vocal | Wendell Phillips Academy DuSable High School |
| This Could Be the Start of Something Big | Written by Steve Allen | Pop | Hyde Park High School |
| Let's Get Together | Tommy Sands | Children's Music | LaSalle Elementary |
| Rawhide | Frankie Laine | Country | Lane Tech High School |
| Bo Diddley (1955 Single Version) [Mono] | Bo Diddley | Rock | Willard Elementary Foster Elementary |
| There Is No Greater Love | Gene Ammons | Jazz | DuSable High School |
| A Change Is Gonna Come | Sam Cooke | R&B/Soul | Wendell Phillips |
| The Congregation | Johnny Griffin | Jazz | DuSable High School |
| Freddie's Dead (Theme from 'Superfly') | Curtis Mayfield | Soundtrack | Wells High School |
| You'll Never Find Another Love Like Mine | Lou Rawls | R&B/Soul | Forrestville Elementary Dunbar High School |
| I'll Take You There | The Staple Singers | Inspirational | Parker High School |
| A Boy Named Sue (Live Version) | Shel Silverstein | Pop | Darwin Elementary Roosevelt High School |
| Don't You Care | The Buckinghams - Carl Giammarese | Rock | Lane Tech High School |
| People Get Ready | The Impressions - Jerry Butler, Curtis Mayfield | R&B/Soul | Washburne and Wells Respectively |
| Summer Nights | Written by Jim Jacobs | Soundtrack | Taft High School |
| Sun Goddess | Ramsey Lewis | Jazz | Wells High School |
| O-o-h Child | The Five Stairsteps - Burke Family | R&B/Soul | Harlan High School |
| Only the Strong Survive | Jerry Butler | Rock | Washburne |
| Listen Here | Eddie Harris | Jazz | Farren and Burke Elementary DuSable and Hyde Park High Schools |
| Chuck E's in Love | Rickie Lee Jones | Pop | Stockton Elementary |
| Oh Girl | The Chi-Lites - Eugene Record | R&B/Soul | Englewood |
| I Feel for You | Chaka Khan | Pop | Kenwood Academy |
| Rockit | Herbie Hancock | Jazz | Hyde Park High School |
| Finishing the Hat | Sung by Mandy Patinkin - from Sunday in the Park with George | Soundtrack | Edward Coles Elementary South Shore High School Kenwood High School |
| City of New Orleans | Steve Goodman | Folk | Volta Elementary |
| The Thanksgiving Song | Fred Holstein | Rock | Hookway and South Shore |
| Soulful Strut | Young-Holt Unlimited - Eldee Young | R&B/Soul | McKinley High School |
| Miss Mary Mack | Ella Jenkins | Children's Music | Phillips Elementary DuSable High School |
| On & On | Jesse Saunders | Dance | Kenwood Academy |
| Renegade | Styx - Dennis DeYoung and James Young | Rock | DeYoung - Bennet and Harlan; Young- Calumet |
| I Believe I Can Fly | R. Kelly | R&B/Soul | Kenwood Academy |
| Black Sunshine | White Zombie - Jay Noel Yuenger | Rock | Harte Elementary Kenwood Academy |
| Be My Love | Von Freeman | Jazz | DuSable High School |
| New African Village | Chico Freeman | Jazz | Parker High School |
| Hey Mama | Kanye West | Hip Hop/Rap | Vanderpoel Elementary |
| And I Am Telling You I'm Not Going (Highlights Version) | Jennifer Hudson | Soundtrack | Dunbar High School |
| Sanford and Son Theme (The Streetbeater) | Quincy Jones | Jazz | Raymond Elementary |
| Um, Um, Um, Um, Um, Um | Major Lance | R&B/Soul | Wells High School |
| Duke of Earl | Gene Chandler | R&B/Soul | Englewood High |
| Raindrops | Dee Clark | Pop | Marshall High School |
| When I Call On You | Kool Gents | R&B/Soul | Marshall High School |
| I Miss You Very Much (feat. Holly Maxwell) | Holly Maxwell | Jazz | Parker High School |
| Baby Love | Mother's Finest - Joyce Kennedy | R&B/Soul | Flower High School |
| Stay by My Side | Jo Ann Garrett | R&B/Soul | DuSable High School |
| Selfish One | Jackie Ross | R&B/Soul | Wentworth |
| Kick, Push | Lupe Fiasco | Hip Hop/Rap | ? |
| Lovin' You | Minnie Riperton | R&B/Soul | Hyde Park High School |
| Beginnings | Chicago - Terry Kath | Rock | Taft High School |