Chuck Cantalamessa Entertainment

Meet Chuck Cantalamessa, singer, songwriter, guitarist, entertainer

Singer / Songwriter / Guitarist

Chuck Cantalamessa is a singer, songwriter, guitarist whose music is a special blend of mellow folk rock … a mixture of country and festive upbeat sounds of the islands. Chuck plays a 12-string acoustical guitar, which provides a percussive sound with rich harmonic overtones. His music career has run the gamut. He has played in ampitheaters in front of more than 10,000 music fans. He and his band were once chosen from over 20,000 applicants to appear on the original talent-based reality show Star Search, becoming season champs. He has opened shows for Fleetwood Mac, The Outlaws, Stephen Stills, Tom Rush, Dave Mason, Firefall, and Huey Lewis & the News to name a few. He has toured extensively throughout the United States and internationally in the Caribbean and Costa Rica. He has performed at thousands of events, from large stages to smaller, yet lively shows at various clubs and other venues, including fundraising events and weddings. Read Chuck’s full bio here, or for more information on his band Wind Star, click here.

Hire singer, songwriter, guitarist Chuck Cantalamessa for your next event

Hire Chuck

A native of Uniontown, PA, Chuck Cantalamessa is a talented performer available for solo performances at public venues and other special events such as weddings, anniversaries, private parties, corporate events, and more. During these engagements he performs a combination of hit songs by hundreds of popular artists (see Repertoire for a list), as well as some of his original compositions (sample some of his music here). Using his charm and outgoing personality, Chuck likes to engage his audience in entertaining discussions, and will also invite the audience to make requests and even jump on stage to sing. Chuck can also perform as a duo with other talented musicians, or with his band Wind Star. For rates and to book a performance, click here.

Sample Chuck Cantalamessa's music

Music Samples

Several of Chuck’s albums, as well as other individual tracks are available to sample for free on the Music Store page. If you like what you hear, you can also purchase the albums or individual tracks digitally for download to your computer. Most of the tracks are performed by Chuck and his band Wind Star, but we’ll occasionally offer several solo recordings, so check back frequently.