1989: La Toya Jackson has appeared on the cover of Playboy 24 times in 15 countries, including twice in the US–once in 1989 and another time in 1991.
17| Marilyn Monroe
1953: Marilyn Monroe, the very first Playboy cover model, has appeared on the cover 22 times in 13 countries, ranging from Romania to Taiwan. Her four American appearances range from 1953 to 2005, with only one being while she was alive.
16| Cindy Crawford
15| Naomi Campbell
1999: Naomi Campbell has appeared on 18 Playboy covers in 16 countries, including her American debut in 1999.
14| Farrah Fawcett
1995: Farrah Fawcett has been featured on 15 Playboy covers in ten countries, including four times in the US. She appeared on American covers between 1978 and 1997, which all coincided with her movie releases.
13| Kim Basinger
1983: Kim Basinger has appeared on 13 Playboy covers in 11 countries, including on the American edition.
12| Joan Collins
1983: Joan Collins has appeared on 12 Playboy covers in 11 countries, including once on the American Playboy in 1983.
1985: Madonna has appeared on Playboy covers in ten countries, including multiple times in Spain.