| Playboy founder Hugh | 20 |
| Playboy founder who injured his calf muscle? | 44 |
| Playboy founder's moolah? | 29 |
| Playboy founder, familiarly | 27 |
| Playboy founder, for short | 26 |
| Playboy head, to friends | 24 |
| Playboy Hugh, familiarly | 24 |
| Playboy Khan | 12 |
| Playboy Khan et al. | 19 |
| Playboy magnate, briefly | 24 |
| Playboy Mansion guy | 19 |
| Playboy Mansion name | 20 |
| Playboy Mansion nickname | 24 |
| Playboy Mansion resident, familiarly | 36 |
| Playboy model ___ Nicole Smith | 30 |
| Playboy nickname | 16 |
| Playboy No. 1 | 13 |
| Playboy of the Western World author | 38 |
| Playboy or Esquire, for short | 29 |
| Playboy or Playgirl-caliber model | 33 |
| Playboy pie | 11 |
| Playboy publisher | 17 |
| Playboy publisher Hugh | 22 |
| Playboy publisher, to friends | 29 |
| Playboy subject | 15 |
| Playboy types, briefly | 22 |
| Playboy types, for short | 24 |
| Playboy's agenda? | 21 |
| Playboy's bunny, e.g. | 25 |
| Playboy's come-on | 21 |
| Playboy's crowd | 19 |
| Playboy's gaze | 18 |
| Playboy's logo | 18 |
| Playboy's look | 18 |
| Playboy's malady | 20 |
| Playboy's plea? | 19 |
| Playboy's request | 21 |
| Playboy's version of a right | 32 |
| Playboy, for one | 16 |
| Playboy? | 8 |
| PlayboyÂ’s wear | 18 |
| Playboys | 8 |
| Playdate lunch option, for short | 32 |
| Playdate participants | 21 |
| Played | 6 |
| Played "Ray" | 22 |
| Played "Taxi" again | 29 |
| Played (around) | 15 |
| Played (with) | 13 |
| Played 18 | 9 |
| Played 18 holes | 15 |
| Played a banjo | 14 |
| Played a bat-and-ball game | 26 |
| Played a bugle | 14 |
| Played a card? | 14 |
| Played a child's game | 25 |
| Played a club, maybe | 20 |
| Played a flute | 14 |
| Played a flute in a march | 25 |
| Played a flute in a march, e.g. | 31 |
| Played a game on ice | 20 |
| Played a good joke on | 21 |
| Played a heart, say | 19 |
| Played a knight game? | 21 |
| Played a Little? | 16 |
| Played a major role? | 20 |
| Played a military flute | 23 |
| Played a pandurina | 18 |
| Played a part | 13 |
| Played a part (in) | 18 |
| Played a part to the hilt | 25 |
| Played a pipe | 13 |
| Played a role | 13 |
| Played a role? | 14 |
| Played a shrill flute | 21 |
| Played a shrill instrument | 26 |
| Played a tape again | 19 |
| Played a tattoo | 15 |
| Played a trumpet | 16 |
| Played again | 12 |
| Played aloud, as a TV | 21 |
| Played an accompaniment | 23 |
| Played an Elizabethan instrument | 32 |
| Played an ice game | 18 |
| Played an old episode | 21 |
| Played an old instrument | 24 |
| Played anew | 11 |
| Played around (with) | 20 |
| Played around with a recorder | 29 |
| Played at love | 14 |
| Played at the park | 18 |
| Played awhile onstage | 21 |
| Played back of the plate | 24 |
| Played badly | 12 |
| Played Ben Cartwright | 21 |
| Played between tours | 20 |
| Played boisterously | 19 |
| Played cat and mouse (with) | 27 |
| Played charades | 15 |
| Played chef to | 14 |