Coming to prominence with the 2001 recording of his Night Sessions album, Botti established a reputation as a versatile musician in both jazz and pop music for his ability to fuse both styles together.

[7] At the age of 17, he ended up at Mount Hood Community College in Gresham, Oregon, by convincing his high school to allow him to fulfill his remaining senior year credits there.

Mount Hood's program was headed by Larry McVey, whose band had come to be a proving ground and regular stop for Stan Kenton and Mel Tormé when they were looking for new players.

[8] Botti was also the recipient of two grants from the National Endowment for the Arts which allowed him to study with trumpeter Woody Shaw and saxophonist George Coleman during two consecutive summer breaks.

Botti's solo debut, First Wish, was released in 1995; his second effort, Midnight Without You, which included a collaboration with Blue Nile vocalist Paul Buchanan, appeared in 1997.

[12] In the late 1990s, Botti was a member of Bruford Levin Upper Extremities, a group exploring a more experimental, jazz fusion-oriented sound than his solo records.

[15] A Thousand Kisses Deep, was released in 2003 and contained a group of originals and covers that accent Botti's crossover appeal as both a jazz and pop musician.

To Love Again: The Duets, released in 2005, continued where the previous album left off with more lush orchestral jazz via the London Session Orchestra, this time showcasing guest vocalists — as well as a handful of instrumental tracks.

The CD and platinum-certified DVD included duets with Sting, Burt Bacharach, Gladys Knight, Jill Scott and Renee Olstead.

The album places focus on Botti's Italian roots through such songs as "Venice", "Estaté", and the title track "Italia", on which he partnered with Andrea Bocelli.

Performing with the Boston Pops Orchestra, Botti shared the stage with Yo-Yo Ma, Steven Tyler, Josh Groban, Katharine McPhee, John Mayer, Sting, and others.

Botti performed "The Star-Spangled Banner" in MetLife Stadium for a crowd of over 80,000 and a worldwide television audience on November 3, 2014, prior to the Indianapolis Colts vs. New York Giants National Football League game.

[27] Botti appeared in the Season 3 The Real Housewives of Beverly Hills episode "Don't Sing For Your Supper" as a dinner guest of Yolanda Hadid and David Foster.