Through the 90's The Mommyheads toured North America extensively and released several albums, the last co-produced by Don Was for Geffen Records.
In 1998, The Mommyheads broke up and Holt released his contemplative folk album "I'm Here With You," featuring just voice and a single nylon-stringed guitar.
Shortly after, he began work on his alternative power-pop album "Pilot Single,"[2] and moved with Simone to her native Toronto.
In Toronto, Holt started a band called The Kids, with bassist Peter Murray, guitarist David Celia, and longtime Ron Sexsmith drummer Don Kerr.
He played and recorded with numerous Canadian artists, including Ron Sexsmith, David Celia, Owen Pallett, Michelle Rumball, Waleed Abdulhamid, The Hidden Cameras, Ronley Teper, Ben Gunning, Wooden Stars, Tanya Philipovich, Brian MacMillan, Karyn Ellis, and Adam Warner.
His 2011 "Make Our Own Culture Tour" consisted of 60 intimate living room gatherings across North America and Europe, featuring a variety of other performers and participatory activities.
In 2014, he co-organized Toronto's First Annual Festival of House Culture, a weekend of theater, music, visual arts, poetry, comedy, film, food, conversations, and workshops, all in people's homes.
In 2015, Holt released "24 Preludes for Piano," a double album of original classical pieces inspired by early 20th Century composers such as Maurice Ravel, Alexander Scriabin, and Erik Satie.