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| Playboy 1999/01 |
|
Number
|
|
541 |
| Cover |
|
Marilyn Monroe |
| Playmate |
|
Jaime Bergman |
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| Playboy 1999/02 |
|
Number
|
|
542 |
| Cover |
|
Pamela Anderson |
| Playmate |
|
Stacy Fuson |
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| Playboy 1999/03 |
|
Number
|
|
543 |
| Cover |
|
Gene Simmons, Robin Sullivan, Jeannie Millar, Tina Charest |
| Playmate |
|
Alexandria Karlsen |
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| Playboy 1999/04 |
|
Number
|
|
544 |
| Cover |
|
Rena Mero |
| Playmate |
|
Natalia Sokolova |
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| Playboy 1999/05 |
|
Number
|
|
545 |
| Cover |
|
Charlize Theron |
| Playmate |
|
Tishara Cousino |
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| Playboy 1999/06 |
|
Number
|
|
546 |
| Cover |
|
Heather Kozar |
| Playmate |
|
Kimberly Spicer |
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| Playboy 1999/07 |
|
Number
|
|
547 |
| Cover |
|
Brooke Richards |
| Playmate |
|
Jennifer Rovero |
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| Playboy 1999/08 |
|
Number
|
|
548 |
| Cover |
|
Nell McAndrew |
| Playmate |
|
Rebecca Scott |
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| Playboy 1999/09 |
|
Number
|
|
549 |
| Cover |
|
Rena Mero |
| Playmate |
|
Kristi Cline |
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| Playboy 1999/10 |
|
Number
|
|
550 |
| Cover |
|
Jennifer Rovero |
| Playmate |
|
Jodi Ann Paterson |
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| Playboy 1999/11 |
|
Number
|
|
551 |
| Cover |
|
Mia St. John |
| Playmate |
|
Cara Wakelin |
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| Playboy 1999/12 |
|
Number
|
|
552 |
| Cover |
|
Naomi Campbell |
| Playmate |
|
Brooke Richards |
