YouTube video

The rotund, bulldog-faced entertainment lawyer starring in his own rap tune is Jay B. Ross.  In his modest office on Grand Ave. and Halsted, the walls are lined with famous portraits and awards. 

He’s been in business for 40 years, an industry pioneer whose music clients have included James Brown, Ray Charles’ family, Muddy Waters, Woody Guthrie estate, Jerry “the Iceman” Butler, Koko Taylor, Gene Chandler, Shirley Jones, Anna Maria Alberghetti, Bonnie Pointer, Debbie Sledge, Albertina Walker and Willie Dixon.   West Side clients past and present include blues and soul performers Dinah Washington, Syl Johnson, Howlin’ Wolf,  Larry “Mud” Morganfield, and Tyrone Davis.

Ross specializes in publishing rights, royalties, licensing, digital money collection; right of publicity, contracts, negotiations, copyrights, incorporations, wills and estates, personal injury.  He’s always looking for clients, prioritizing those who can pay up front because legal expenses are so unpredictable in entertainment. Getting access to legal help is a a problem that remains unsolved for many blues musicians. They come from poverty backgrounds and continue to make very low wages.

“Rappin’ lawyer, he’s the one with a lot of clout, ” sings Jay in a deep monster-like voice.  A hilarious chorus of clients echoes,  “Rappin lawyer, he’s the one who can help you out.”   Ross and Farley Jackmaster Funk wrote the tune, named “Sue the Bastards.’  In the video the rappin’ lawer vows to make a deal for his clients, and if that doesn’t work, take the matter to the Supreme Court.  Dressed as judges in somber black robes, rapping along, are Jerry Butler and Gene Chandler among others  (you have to see it).

Why did Ross get the idea to rap in a video?  He notes the music business has changed rapidly, with new wrinkles like digital royalties unheard of even 15 years ago. “I like to know the inside of the business. One of the ways to know the pitfalls for a performer is to be a performer yourself.”  He’s even going through the process of submitting the video for a Grammy award, just to see what that’s about.  

Ross shares his vast experience by teaching at local colleges and law schools including Kent School of Law and Columbia College. His Jay B. Ross Foundation promotes education and networking in Chicago’s entertainment industry.  Ross has served on committees of Chicago Bar Association,  National Association. of Independent Record Distributors, NARAS ( Grammy organization), Rhythm and Blues Convention, Billboard magazine, MIDEM.  Besides lawyering, he has helped artists make connections, promoting Chicago house music worldwide in the1980s.

Ross jokes that he’s “the world’s oldest living rapper,” in a WGN TV interview

On Jay B. Ross’s website you can find helpful negotiating hints, plus a fascinating series of videos with some of his well-known clients.   

The Rappin’ Lawyer—along with West Side blues singers Mud Morganfield and Larry Taylor— will perform in a tribute to Willie Dixon, organized by Dixon’s granddaughter, music entrepreneur Tomiko Dixon, from 4 to 8 p.m. on Thursday June 30, at Blues Heaven, 2120 S. Michigan Av.


"Barrelhouse Bonni" McKeown, the author of "West Side Blues Blog," has played piano and written about blues music for over 15 years.  She has led classes for young and old on...