The design of the album is intended to ape the poor production values offered by contemporary bootleg records, even going so far as to give an incorrect track listing: the song "Draw the Line" is included on the record but does not appear listed; the track is a secret track after "Mother Popcorn". The album also features a secret live instrumental cover of "Strangers in the Night" inserted into their cover of "Train Kept A-Rollin'", which was probably a nod to a similar quote by Jimi Hendrix during "Wild Thing" at the Monterey Pop Festival. The back of the CD cover includes two coffee stains over the picture of Joe Perry playing before a live audience. The original LP cover had the coffee stains, but not the picture of Perry, which was part of the gatefold artwork. The record also features one of Aerosmith's first live versions of The Beatles "Come Together", which they performed in the 1978 movie Sgt. Pepper's Lonely Hearts Club Band, and the first record appearance of Richie Supa's "Chip Away the Stone" (the studio version of this song would later be released on 1988's Gems compilation).
In the band memoir Walk this Way, Perry recalls, "I didn't want to do a live album at the time because there were so many perfect live albums coming out, all doctored and fixed and overdubbed. Big deal. Double live album - 'standard of the industry'. I felt like we had to avoid that and do a real live album like Live at Leeds or Get Yer Ya Ya's Out or that old Kinksalbum." In his own 2014 memoir Rocks, Perry confessed that the idea behind the LP confounded their label Columbia:
We were working on Live! Bootleg!, an album of old shows that we intentionally wanted to sound bootlegged. A couple of those tracks were recorded off air onto a cassette. It had hiss all over it. We left on the hiss because the hiss was real. But I'm not sure Columbia ever understood our concept. They wanted a clean sound, but we wanted to keep it real. That's the thrill of a real bootleg.