Late in his school career, Toro y Moi formed a close musical relationship with fellow chillwave artist Ernest Greene, who performs under the name Washed Out.

[10] In mid-2009, Bear was signed to Carpark Records,[11] on which he released his debut Toro y Moi full-length album, Causers of This, in January 2010.

Underneath the Pine marked a stylistic departure from the previous album in that it was made up of all live instrumentation and contained no samples.

Bear cites horror movie soundtracks, space disco, and film composers Piero Umiliani and François de Roubaix as inspiration for the album's sound.

"[16] In an interview with the website At the Sinema, he suggested that he had moved beyond the chillwave genre: "All that stuff is really good music, like Ernest Green (Washed Out) and Neon Indian.

"[17] On September 13, 2011, Toro y Moi released an EP titled Freaking Out, featuring a cover of "Saturday Love" by Cherrelle and Alexander O'Neal.

"[22] The album was called "highly indebted to the late sacrosanct hip-hop producer J Dilla" by the San Francisco Bay Guardian.

The band added Bay Area multi-instrumentalist Brijean Murphy on congas, and were joined by The Mattson 2 to play the song "JBS".

Tracks like "Ordinary Pleasure" and "Freelance" showcase the continued funk, disco, and house influence that is woven through the entire Toro y Moi discography.

"[31] A week after the release of Outer Peace and while on tour supporting the album, Bear shared a Dropbox link to a cassette bounce of his mixtape, Soul Trash.

[35] On January 26, 2022, Bear announced his seventh studio album as Toro y Moi, Mahal, alongside the release of its first two singles, "Postman" and "Magazine".

[37] The album took a new stylistic approach compared to his previous work, incorporating elements of emo rap and choral music,[38] and inviting a number of collaborators, including Don Toliver, Porches, Kevin Abstract and Benjamin Gibbard.

[39][40] Bear stated that Les Sins "was just another way to make weirder music without having to feel I'm alienating Toro y Moi [fans].

StreetView's release was accompanied by the debut of an immersive website, plum.link, that paired streaming of the album with drone footage and effects that enhanced the experience of the music.

Star Stuff was released on Company Records on March 31, 2017, and subsequently reached #1 on the contemporary jazz Billboard Charts.

[45] While touring together in support of Star Stuff, Bear and the Mattson 2 performed their collaborative album alongside existing songs from Toro y Moi's catalog.

Bear has had solo shows in at New Image Art (Los Angeles), FISK Projects (Portland), and Gallery Commune (Tokyo).