[3] Friedman spent his last five years in New York working as a guitarist with the busy show band City Limits, featuring Richard Lanham, former vocalist for The Drifters.

Billed as "Josh Alan," he barnstormed the state of Texas for 20 years, rocking whole arenas with his Guild D-40 and earning three Dallas Observer Music Awards for Best Acoustic Act.

Josh Alan has recorded and/or played with Sara Hickman, Keb' Mo', Kinky Friedman, Bugs Henderson, Phoebe Legere, and was a perennial opener in Texas for dozens of rock and blues acts, including Johnny Winter, Clarence "Gatemouth" Brown, War, Huey Lewis and the News, Bad Company, Mitch Ryder, Michael Nesmith and Wanda Jackson.

[5] Concurrently, Friedman worked as a stringer for Soho News, contributing celebrity profiles, notably of legendary songwriter Doc Pomus.

Just by hanging around him, I felt like he taught me how to write songs…that's what turned me from being a frustrated songwriter into a songwriter.”[2] During this period, Friedman's comix collaborations with brother Drew were gaining momentum.

Beginning with a notorious parody of The Andy Griffith Show, first published in School of Visual Arts instructor Harvey Kurtzman's student publication, Kar-tunz' (later reprinted in RAW magazine), the Friedmans developed an enthusiastic following for their bizarro parodies and dissections of forgotten B-list entertainers and obscure pop culture figures.

With their acidic, occasionally fantastical biographies of second- and third-tier celebrities, such as talk show host Joe Franklin ("The Joe Franklin Story," High Times, June 1981), Wayne Newton ("The Living History of Wayne Newton," High Times, September 1983), Frank Sinatra, Jr. ("The Saga of Frank Sinatra, Jr.," National Lampoon, October 1985) and Joey Heatherton ("I, Joey Heatherton," National Lampoon, December 1989), the Friedman Bros. became the most-feared names in satirical cartooning.

In 2008, Tell the Truth Until They Bleed: Coming Clean in the Dirty World of Blues and Rock 'n' Roll was published by Backbeat Books.

[13] Paul Stone's unfinished adaptation of Tales of Times Square and Kevin Page's documentary on Josh Alan's life, Blacks and Jews, have played film festivals.