 
		
| Date | Cover model | Centerfold model | Interview subject | Pictorials | 
|---|---|---|---|---|
| 1-1966 | Patti Reynolds | Judy Tyler | Princess Grace | |
| 2-1966 | Sissy | Melinda Windsor | Federico Fellini | |
| 3-1966 | no cover model | Priscilla Wright | Bob Dylan, Panel on Crisis in Law Enforcement | |
| 4-1966 | Cynthia Maddox | Karla Conway | George Lincoln Rockwell | |
| 5-1966 | Allison Parks | Dolly Read | Arthur M. Schlesinger, Jr. | Allison Parks - PMOY | 
| 6-1966 | Mary Warren | Kelly Burke | Mike Nichols | |
| 7-1966 | Penny James, Patti Reynolds, Joann Russell, Barbara Shaw, Joey Thorpe | Tish Howard | Ralph Ginzburg | Ursula Andress | 
| 8-1966 | Sissy | Susan Denberg | H. L. Hunt | Jane Fonda | 
| 9-1966 | Dianne Chandler | Dianne Chandler | Timothy Leary | Jocelyn Lane | 
| 10-1966 | Penny James | Linda Moon | Mel Brooks | Ann-Margret | 
| 11-1966 | Sue Batchelor | Lisa Baker | Norman Thomas | |
| 12-1966 | Nancy Gould | Susan Bernard | Sammy Davis, Jr. | 
 photo of Playboy 1966
photo of Playboy 1966
 video of Playboy 1966
video of Playboy 1966
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