Crosby joined The Byrds in 1964. The band notably gave Bob Dylan his first number one hit in April 1965 with "Mr. Tambourine Man." Crosby ultimately appeared on the band's first five albums, and produced the original lineup's 1973 reunion album. In 1967 he joined Stephen Stills of Buffalo Springfield on stage at the Monterey Pop Festival, shortly after the duo began to form Crosby, Stills & Nash in 1968 with Graham Nash of The Hollies. After the release of their debut album CSN won the Grammy Award for Best New Artist of 1969. Neil Young joined the group for live appearances, their second concert being Woodstock, before recording their second album Deja Vu (Crosby, Stills, Nash & Young album). Meant to be a group that could collaborate freely, Crosby and Nash recorded 3 gold albums in the 1970s, while the core trio of CSN remained active from 1976 until 2016. CSNY reunions took place in each decade from the 1970s through the 2000s.
Notable songs Crosby wrote or co-wrote include "Lady Friend," "Why," and "Eight Miles High" with the Byrds and "Guinnevere," "Wooden Ships," "Shadow Captain," and "In My Dreams" with Crosby, Stills & Nash. He wrote "Almost Cut My Hair" and the title track "Déjà Vu" for Crosby, Stills, Nash & Young's 1970 album. He is known for his use of alternate guitar tunings and jazz influences. He has released six solo albums, five of which have charted. Additionally he formed a jazz influenced trio with his son James Raymond in CPR (band). Crosby's work with The Byrds and CSN(Y) has sold over 35 million albums.
Crosby has been inducted into the Rock and Roll Hall of Fame twice: once for his work in The Byrds and once for his work with CSN. Five albums he contributed to are included in Rolling Stone's 500 Greatest Albums of All Time, three with the Byrds and two with CSN(Y). He is outspoken politically and has been depicted as emblematic of the 1960s' counterculture.