Richards began his career as the lead singer of the alternative rock band Dishwalla. The band released their debut album Pet Your Friends in 1995. The album scored Dishwalla a hit in 1996 with the Richards-penned "Counting Blue Cars". The song is well known for its lyrics, "Tell me all your thoughts on God, 'cause I'd really like to meet Her". Richards won a Billboard Music Award for Top Mainstream Rock Track of the Year. Along with two Gold and Platinum albums, JR also won two ASCAP Awards for both having the Most Performed Song of The Year.

Dishwalla produced four other albums with Richards as lead singer and main songwriter, including And You Think You Know What Life's About in 1998, a live album called Live... Greetings from the Flow State and the 2002 album, Opaline. After Dishwalla completed their last album with Richards, Dishwalla in 2005, both bassist Scot Alexander and drummer Pete Maloney left the band. The band broke up shortly after their departures. In 2008, Dishwalla reformed with some original members returning and a new lead singer Justin Fox.

Richards’ debut solo album A Beautiful End was released in 2009 and debuted in the Top 50 on iTunes. In 2016, Richards released his second solo album, Honore et Amore, as well as an all-acoustic album of songs he wrote while in Dishwalla, Stripped. Richards has released two albums since the holiday EP "Angelgold " in 2018 and an album of covers called "Under The Cover" in 2019. JR is currently working on his 10th album to be released in 2020