Weiss was born in Iowa City, Iowa, on November 8, 1981. When he was three, he began taking lessons at the Preucil School of Music there. As a child, he moved with his family to Lyndhurst, Ohio, near Cleveland, and studied at the Interlochen Arts Camp from 1991 to 1995 and at the Cleveland Institute of Music with Paul Schenly from 1995 to 2000. Weiss moved on to the Juilliard School in New York, studying with Emanuel Ax and earning a bachelor's degree in 2004. By that time, his career as a performer was already well underway. Weiss made his debut with the Cleveland Orchestra in 1999, performing Liszt's Piano Concerto No. 1 in E flat major, and the following month he replaced an ailing André Watts in a performance of Shostakovich's Piano Concerto No. 2 with less than 24 hours' notice. He was immediately invited back, and he has gone on to perform with many major American orchestras, including the Chicago Symphony, the Philadelphia Orchestra, and the Los Angeles Philharmonic. Weiss made his solo recital debut at Alice Tully Hall in New York in 2004, and the following year, he played in Europe for the first time, at the Louvre in Paris. In 2012, he appeared at Washington's Kennedy Center. He has toured China with the Pittsburgh Symphony and Israel with the Israel Philharmonic under Itzhak Perlman. An enthusiastic chamber music player, Weiss has appeared under the auspices of the Chamber Music Society Two program at Lincoln Center and other major chamber music venues.
Weiss made his recording debut in 2005, backing a recital by cellist Julie Albers. He has recorded mostly for the Naxos and Bridge labels, with one highlight being a 2012 Naxos release of Gershwin piano works with the Buffalo Philharmonic Orchestra under conductor JoAnn Falletta. In 2021, Weiss joined The Orchestra Now and conductor Leon Botstein on the Bridge album Piano Protagonists. Weiss often travels to Colombia to serve as an instructor at the Red Esquela de Música Festicámara Medellín. ~ James Manheim, Rovi