Almost 25 years before Sabrina Carpenter was born, Carly Simon was in a department store in New York and feeling pretty good. She’d just released her fifth album, Playing Possum, and the frisky single “Attitude Dancing” was looking to follow her hits “You’re So Vain,” “Haven’t Got Time for the Pain,” and “Anticipation” onto the radio. Then, a woman who was apparently familiar with the cover of Playing Possum approached her.

“She’d either seen a picture of it, or she knew someone who had the album,” Simon recalls. “And she said, ‘What were you thinking?’ Voices were raised.”

Last week, Carpenter unveiled the now-notorious cover for her upcoming album Man’s Best Friend, in which she’s depicted kneeling on the ground, one hand extended toward a figure in a suit who’s grabbing her hair. Debates, some pretty intense, ensued about whether the photo signified savvy, knowing female empowerment or simply empowered the male gaze.

But as Simon well knows, the sight of a female pop star in a similar pose and pushing plenty of the same buttons didn’t start with Man’s Best Friend. Released in 1975, Playing Possum sported a couple of suggestive song titles, like “Are You Ticklish” and “Love Out in the Street,” but its most provocative aspect was its black-and-white cover photo: Simon, on her knees, looking fierce and mysterious in a black negligee and black boots, fists clenched, face partly hidden, mouth sightly open. Photographer Norman Seeff’s shot was the polar opposite of the cover of her previous album, 1974’s Hotcakes, which featured a smiling and visibly pregnant Simon. Of Playing Possum, Simon says, “I remember thinking, if this works, it’ll also let people see that I’ve gotten my body back.”

But in a scenario that may be familiar to the Carpenter camp, fans and feminists alike didn’t know what to make of it and began arguing over its message. As Rolling Stone reported at the time, the Sears department-store chain, which sold a good deal of LPs, considered not carrying Simon’s album at all. Crawdaddy, a competing counterculture magazine, published a review that was entirely devoted to analyzing the cover instead of the music. The image became so indelible that the negligee Simon wore was included in her exhibit at the Rock & Roll Hall of Fame when she was inducted in 2022.

Given how much Playing Possum‘s cover contrasted with Hotcakes, its back story is ironic: It actually began with Simon’s daughter Sally, who, only a few months old, was in a baby carrier on her mother’s back as Simon shopped in Bloomingdale’s. “I was looking through the racks of undergarments, and she bent over with me as I bent over to look at something,” Simon says, recalling how her daughter grabbed at the black lingerie and pulled it into the carrier with her. “It wasn’t noticed at checkout.” (These were the days before security tags were affixed to clothing.)   

When Simon arrived at Seeff’s L.A. studio for the photo shoot, she was wearing the purloined piece of clothing underneath a skirt and blouse. As Simon remembers, she was in a dressing room putting her street clothes back on after the session when she heard Isaac Hayes’ “Theme from Shaft” playing in the studio. “I loved that song, so I ran out and started dancing to it,” she says. As Seeff clicked away, Simon, in the black lingerie, sang along with Hayes, ultimately lying down on the floor on her back before pulling herself up. “And that’s when Norman took that picture, after I landed in that pose,” she says. “It wasn’t done on purpose. It wasn’t a setup.”

When the photos were developed, Seeff zeroed in on one in particular. “I’m looking at these shots, and I go, ‘Well, here’s a shot that’s got some kind of energy to it,'” he says. “The head’s cut off. She was in movement from being on the floor to standing up, and she’s got this clenched fist. No one thought about what it might convey. It was a fascinating, unique image and it left a lot to the imagination.” Related Content

Simon herself wasn’t sure at first but came around to the same thinking. “There was something about black and white photographs, where you suddenly see it as an art picture,” she says. “The whole thing looked artistic, even though it wasn’t artistic on purpose.”  

In Simon’s memory, the initial feedback she received — from then husband James Taylor and her producer, the late Richard Perry — was positive, and she proudly showed it to Joni Mitchell and Graham Nash at a birthday party Simon threw for Taylor in L.A. just before the album was released. “Everybody looked at it, and people definitely had a reaction to it,” she says, “but they wouldn’t have told me what they really thought.”

The more visceral responses arrived when Playing Possum was shipped to stores. “How’s that for crashing the image of the sweet mother-to-be beaming on the cover of her last album?” wrote one critic. Another wondered if she should be carrying a whip to match the outfit. Simon even recalls her mother, Civil Rights activist Andrea Louise Heinemann, saying, “Carly, darling! What are you doing?”

“Suddenly, I’m getting calls from Time and Newsweek, saying, ‘This is one of the sexiest covers that has ever known,'” Seeff says. “There’s this whole controversy around what did it represent? It felt very much like that energy in a woman, but I just thought of it as a beautiful shot. None of that stuff they were talking about was the intention.” The conversation didn’t hurt sales: Playing Possum became Simon’s third straight Top 10 album.

The cover of Carpenter’s Man’s Best Friend isn’t an overt homage to Playing Possum, but Simon has been recognized by modern pop stars. Both Carpenter and Olivia Rodrigo have covered “You’re So Vain” onstage, and Addison Rae shouted out Simon’s later Boys in the Trees album in a recent interview. “I love it that the younger girls are discovering me, and that I’ve had attention from them,” Simon says.

Of Carpenter’s controversial artwork, Simon doesn’t quite see the fuss. “She’s not doing anything outrageous,” she says. “It seems tame. There have been far flashier covers than hers. One of the most startling covers I’ve ever seen was [The Rolling Stones’] Sticky Fingers. That was out there in terms of sexual attitude. So I don’t know why she’s getting such flak.”

Simon herself hasn’t released a new album since 2009, but she’s been working on new music on and off for a decade. The songs, many produced by her son Ben, include “Howl,” featuring Nile Rodgers on guitar and a guest vocal from Chris Stills, son of Stephen. “It’s kind of a vengeance song about getting back at someone, or, in this case, a whole lot of people,” she says. “Is it tender? No, it’s not. It’s very gutsy. It’s got a lot of power.” She’s also written a song about her daughter Sally, “Mother of Pearl,” and another, “Do It Anyway,” that she calls “kind of a coach song — ‘if you think you can’t do it, do it anyway.’” “Pity the Poor Man” was co-written with Natasha Bedingfield, and Simon has also set a W.H. Auden poem to music.

What form the songs will take remains to be seen, Simon says. “I didn’t record it as an album,” she says. “I just did it as a song here and a song there. We have 10 songs, an album’s worth, but you don’t really release albums now, so we’re just going to release one by one.”

Since it may not be an actual old-fangled album, Simon isn’t even thinking about cover art. But as far as advice to Carpenter on how to deal with her situation, Simon says, “Well, any press is good press, so I wouldn’t worry about the press. And as far as her being salacious, I certainly don’t think it’s that. I mean, look at all of the people who dress much more scantily. She’s so beautiful, and she should be proud of herself and the way she looks. I don’t see anything wrong with that.”

Taking another look at Man’s Best Friend, Simon has one last thought. “I thought it was going over the line a little bit, touching the man’s knee,” she says, with a chuckle. “I thought she didn’t have to do that.”