Songfacts®:

• Frontman Chris Robinson told Rolling Stone magazine that this country ballad is "one of the best things Rich (Robinson, guitar) and I have ever written."
• Chris Robinson (from The Black Crowes Bootleg Project): "It's probably the song I'm most proud of on this album. The last verse sums up a lot ['It's too late to play it safe/So let's let it all ride']. That's our attitude. There's no reason for anybody here to ever hold back. We're doing this full bore, and it's gonna be open. I always thought our best writing was our ballads. People want to identify the Black Crowes as this guitar band - which we are - but I think 'Oh Josephine' is the quintessential Black Crowes song, and the coda at the end says, 'We know who we are.' It's one of those songs you can put on at 5:30 in the morning and decide whether you're going to keep going or put it down for the night."
• The dueling guitars at the end of this track were played by Rich Robinson and Luther Dickinson of the North Mississippi Allstars, who officially joined the Crowes with this album. Robinson and Dickinson had already worked together on their side project, Circle Sound, a covers-jam band, in early 2007. Robinson's brother, Chris told Rolling Stone with a smile: "Hey, we're the Black Crowes. We gotta tack on a 3-minute coda."