The obvious question is who Stella Blue was. No one knows. Because of the September 2019 death of Dead lyricist Robert Hunter, who wrote the words for this one (Jerry Garcia did the music), we'll likely never know. Maybe that's for the best.
It's a sad song. Some have speculated that the "blue" is meant in the sense of the blues, being bummed and broken down. The song doesn't seem to be about lost love but rather meditations on the transience and seeming meaninglessness of life.
And when you hear that song
come crying like the wind
it seems like all this life
was just a dream
One note Hunter did elect to leave us is found in Box of Rain, his book of lyrics. In there he says simply that he wrote this song in the Chelsea Hotel in 1970, which makes the Chelsea one of the "blue-light cheap hotels" mentioned in the song.
Over the years, New York City's Chelsea Hotel has figured into many songs and is a sort of musical landmark. In the late '60s and early '70s, it was the extended home of the Dead, Leonard Cohen, Bob Dylan, Joni Mitchell, Tom Waits, and many others.
In the Italian language, "stella" means "star."
The Dead first performed this song live at the Hollywood Bowl in Los Angeles, California, on June 17, 1972. They played it live a total of 328 times. The final show came at Maryland Heights, Missouri's Riverport Ampitheatre on July 6, 1995.
David Dodd at Dead.net
, a true Dead scholar if there ever was one, thinks "Stella Blue" may represent the apex of the songwriting partnership between Hunter and Garcia.