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Classics
Miss June Is Here—And She’s a True Work of Art Gabrielle Richardson, the model and art gallery owner, is our Playmate of the Month.
Our Miss June 2026 is a work of art, but one beautiful painting never feels like enough. We were so inspired by Gabrielle Richardson that we couldn’t let her be a standalone exhibit. So, we looked at Miss Junes past from our 1990s archives to flesh out the full museum. As it turns out, Playboy often launched our Playmate of the Year in June in the ’90s, so we compiled a list of some of our most iconic cover stars from that decade. The result? A feast for the eyes worthy of the Louvre.
1991 PMOY: Lisa Matthews
Photos by Stephen Wayda.
1992 PMOY: Corinna Harney
Photos by Richard Fegley.
1993 PMOY: Anna Nicole Smith
Photos by Daniela Federici
1994 PMOY: Jenny McCarthy
Photos by Richard Fegley.
1995 PMOY: Julie Lynn Cialini
Photos by Stephen Wayda
1996 PMOY: Stacy Sanches
Photos by Stephen Wayda.
1997 PMOY: Victoria Silvstedt
Photos by Stephen Wayda.
1999 PMOY: Heather Kozar
Photos by Arny Freytag
