In 1995 Vieaux began a stint as an official Arts Ambassador of the U.S. in Southeast Asia, touring Myanmar, Cambodia, Thailand, Laos, India, Nepal, and Bangladesh. Following this appointment, he launched a 53-city tour of the U.S. and France, and ever since then he has been in demand as a recitalist. In 1997 he began teaching at the Cleveland Institute of Music, his alma mater, and in 2001 he was a founder of the guitar department at the Curtis Institute of Music in Philadelphia. Vieaux was also a pioneer in developing formal guitar instruction over the Internet, establishing the Jason Vieaux School of Classical Guitar on the ArtistWorks platform in 2012.
Vieaux released his first album, a collection of Spanish guitar music, on the Naxos label in 1996. He won the Grammy Award for Best Classical Instrumental Solo in 2015 for his album Play. He signed with Cleveland's Azica label, releasing an album of guitar sonatas by Manuel Ponce in 2001, and since then has recorded mostly for that label. Vieaux has issued music by the tango-classical crossover composer Astor Piazzolla and by jazz guitarist Pat Metheny in addition to traditional repertory. He has performed concertos with nearly 100 orchestras around North America, and he has collaborated with the Escher String Quartet and with harpist Yolanda Kondonassis. A supporter of new music, he has premiered works by Keith Fitch, Vivian Fung, Dan Visconti, David Ludwig, and other contemporary composers.