“"World class, soulful, I-got-chills live music... Holly is a performer who gives us all the feels."”

— Southern Oregon Magazine

Holly Gleason

Americana's Sweetheart

Holly Gleason, a sing-songwriter from Monterey, CA, has just released her long-awaited follow up album TRIPPING INTO WONDERFUL – a spiritually uplifting journey through Americana music. Her Django Reinhardt inspired single, “L’Histoire de l’Amour,” can be heard on the airwaves of Southern Oregon’s NPR affiliate Jefferson Public Radio, while the album explores multiple music avenues, unapologetically mixing genres while maintaining her characteristic indomitable optimism. 

Holly’s debut album "Light Show" is a collection of romantic songs that speak with sweet and sour levity combined with humble and refined self-reflection, luring the listener from quirky pillow talk to soul-wrenching heartache in one sentence. Her beautiful-to-brass style of singing around artisanal guitar playing is raw, sincere, and elegantly self-effacing.  You can find her music, including the upbeat single “Getting Better” on Spotify, iTunes, and Amazon Music.

Press photos

Music

Video

explore music

Inquiries

Complete Bio

Holly Gleason grew up in the timeless, symphonic mists of coastal Monterey, CA. After obtaining a Fine Arts degree from the University of Southern California she worked in Hollywood as an actress for a few years, appearing on General Hospital and in several national commercials. After a transformative trip to Europe Holly found her voice as a composer and began a prolific decade of non-stop songwriting.

 

Mz. Gleason emerged onto the LA club scene singing an eclectic mix of original songs and grabbed the attention of start-up music company My Record Label’s™ creator Travis Allen who awarded her a production deal for her first single release "Treasure," as a promotional campaign for the website's launch. The song appears on Harriet Schock's LA WOMEN IN MUSIC- SOIREE Compilation Album alongside some of Los Angeles' most notable female indie artists.

 

She moved to the live-music-centric Rogue Valley of Southern Oregon in 2015 and paired up with multi-instrumentalist Jeffrey ("Dr. J") Judkins who built a recording studio to produce her long-awaited second album release, TRIPPING INTO WONDERFUL, scheduled to release in spring 2026. The album features long-time musical friends and bandmates JD Berlingieri, Jim Sitter, Gary Dunsmoor and Rogue-Valley legend Nick Garret-Powell. The album drastically switches gears from the melancholic LIGHT SHOW, while still having a soul-searching tone TRIPPING INTO WONDERFUL is much more effervescent, eclectic, and power-packed with a wider range of musical styles from classic rock to gypsy jazz.  

Holly resides currently in Dunnellon, FL where she is working on her next project- an inspired musical book for children.