39/Smooth is the only album by Green Day to feature John Kiffmeyer on drums. It was released in 1990, with its first releases being black vinyl. It was then made in green vinyls, with only 800 existing. Old versions of the album have the old Lookout! Laytonville address printed on the back.
Only 3,000 copies of the album were sold when it was first released. After the release of Dookie however, sales went up to 55,000 copies.
Jesse Michaels of the Berkley punk rock band, Operation Ivy, contributed the artwork of the album. The inner sleeve features lyrics written by Billie Joe Armstrong and letters by Kiffmeyer and Lookout! owner, Larry Livermore that were addressed to I.R.S. Records that rejected their offer to sign Green Day to the label.
The album's title is named after Armstrong's older brother and a "stoner thing" between Mike Dirnt and himself. "39" was because that's how old his brother was at the time of recording. Armstrong and Dirnt could not decide between both "39" and "Smooth" and decided to combine them together.