Weiss was born in New York City, but began his musical studies in earnest by attending North Texas State University. He graduated in 1986 and returned to New York. He soon found work with Jaki Byard, Frank Foster, and Jimmy Heath and began to study with fellow trumpeters Tommy Turrentine and Bill Hardman. He also attended Barry Harris’ weekly workshops, a valuable learning experience for Weiss and an opportunity for him to play with Mr. Harris and Walter Davis Jr.
Weiss also began leading the “After Hours” jam session at the Blue Note with many of the up and coming musicians of the day including Stephen Scott, Winard Harper, Leon Parker, Sam Newsome, Justin Robinson, and Rodney Kendrick. Among the musicians he performed with during his tenure were Roy Hargrove, Clifford Jordon, Mulgrew Miller, Jeff Watts, Terence Blanchard, Benny Green, and Billy Hart. In 1990, Weiss formed a band with tenor saxophonist Craig Handy and began performing in various clubs around New York. The bands various personnel included Benny Green, Stephen Scott, or Dave Kikoski on piano, Christian McBride on bass, and Billy Hart or Je? Watts on drums. Weiss also assisted Handy with music to the NBC series “The Cosby Mysteries” and arranged the main theme for the show. Weiss began getting more calls for his arranging and transcribing skills.
His arrangements/transcriptions have appeared on over 80 CDs. Highlights include CDs by Abbey Lincoln, Freddie Hubbard, and Rodney Kendrick, Alto Legacy with Phil Woods, Vincent Herring, and Antonio Hart, and a Rahsaan Roland Kirk tribute CD entitled Haunted Melodies featuring Joe Lovano, Donald Harrison, James Spaulding, and many others. Weiss also arranged the music and performed on a series of tribute concerts to trumpet greats Freddie Hubbard, Booker Little, Clifford Brown, and Lee Morgan at Birdland, Dizzy’s Club Coca Cola, and Iridium in New York City. The personnel included fellow trumpeters Tom Harrell, Nicholas Payton, Roy Hargrove, Randy Brecker, Terell Sta?ord, Brian Lynch, Eddie Henderson, and Claudio Roditi and rhythm section greats Pete LaRoca, Jimmy Cobb, and Idris Muhammad.
In 1996, recognizing a lack of serious new jazz writing, Weiss recruited some young, first-call New York musicians and composers to form the New Jazz Composers Octet. With their passionate rendering of thoughtful arrangements and firm rooting in tradition, the collective quickly established itself as the “sound of the new jazz mainstream” (Ben Ratliff, NYTimes) and was praised for their ability to “stretch hard bops kind-of-unstretchable formula (Jim Macnie, Village Voice). Of Weiss’ contribution to the Octet’s 1999 recording debut, First Steps Into Reality (Fresh Sound Records), Willard Jenkins commented, “a skilled arranger, transcriber and all-round coordinator, Weiss also brings righteous trumpet chops to this potent mix.” (Jazz Times). The CD was also lauded as a “gem” and received a Critic’s Pick as one of the Top 5 Albums of the Year in Jazz Times