Recognized as one of the top record producers in the United States during the late 1960s and the 1970s, some of Simon's most well known work includes the Band’s Music from Big Pink, The Band, and The Last Waltz,[2][3] Cheap Thrills by Big Brother & the Holding Company featuring Janis Joplin, Songs of Leonard Cohen by Leonard Cohen, and Child Is Father to the Man by Blood, Sweat & Tears.
[5] Simon enrolled at Princeton University where he wrote three more musicals and continued his role as a bandleader, taking a band to the finals of the 1st Georgetown Intercollegiate Jazz Festival.
With the success of "Red Rubber Ball", Simon was assigned other pop music artists like Frankie Yankovic, "America’s Polka King", and jazzman Charles Lloyd.
After that, he was asked to produce an album for Janis Joplin and her band Big Brother And The Holding Company (Cheap Thrills, which featured the hit single "Piece Of My Heart").
[4] While producing an album for the Electric Flag, he met blues artist Taj Mahal, beginning a musical association which continues to the present.
[4][6] He was also the music director for the Last Waltz concert and contributed as a musician to Stage Fright and Islands and produced, played on, and cowrote for their 1990s comeback album Jericho.
In the Eighties, he wrote two ballet scores for the choreographer Twyla Tharp[8] and composed circus music for aerialist Philip Petit (after his solo walk between the World Trade Towers).
Loveheart, wrote and performed a cabaret act called Alone Together For The First Time Again and, more recently, co-authored a popular play, Jackass Flats, which had its professional premiere in June 2011.
These days he performs his own material in concerts on rare occasions, but plays piano weekly with his jazz trio in his hometown near Woodstock, New York and in Melbourne, Florida in a group led by bassist, Ron Pirtle.