By all accounts, none of this was planned, and when the session began her skimpy black teddy was entirely covered. But with the wine flowing in Seeff's studio, and Isaac Hayes' "Shaft" playing on the sound system, Carly began dancing and lost herself in the moment. Later, when she and her manager, Arlyne Rothberg, looked across the contact sheet at a succession of the photos, they both landed on this particular shot: "that's it!". The shot fits with the album's title, at least insofar as it is playful, and it fits even better with the album's first single, "Attitude Dancing", which urges listeners to find their own groove (even if that takes finding a new attitude).
In subsequent years, Playing Possum has regularly featured in rankings of the best-ever album covers, and this makes it all the more maddening that when Elektra Records finally released it on CD, in the 1990s, the cover was so carelessly printed that the top of Carly's head was cut off (see the image below). That is no way to treat a landmark album, and especially one that, initially at least, was greeted with as much dismay as appreciation.