| Play the stoolie | 16 |
| Play the stock market | 21 |
| Play the slots, e.g. | 20 |
| Play the slots | 14 |
| Play the siren | 14 |
| Play the shrinking violet | 25 |
| Play the sax, say | 17 |
| Play the role of | 16 |
| Play the role | 13 |
| Play the roaring game | 21 |
| Play the ribber | 15 |
| Play the recorder, say | 22 |
| Play the raconteur | 18 |
| Play the quibbler | 17 |
| Play the quarterback | 20 |
| Play the private eye | 20 |
| Play the prima donna, e.g. | 26 |
| Play the ponies | 15 |
| Play the point spread, e.g. | 27 |
| Play the piccolo | 16 |
| Play the philanthropist | 23 |
| Play the peeping Tom | 20 |
| Play the peacemaker | 19 |
| Play the pawnbroker | 19 |
| Play the part of | 16 |
| Play the part | 13 |
| Play the paragon? | 17 |
| Play the paraclete | 18 |
| Play the Old Vic | 16 |
| Play the odds | 13 |
| Play the nags | 13 |
| Play the market | 15 |
| Play the lounge lizard | 22 |
| Play the lottery | 16 |
| Play the leading role | 21 |
| Play the leader of the Knights of the Round Table? | 50 |
| Play the lead role | 18 |
| Play the lead | 13 |
| Play the kazoo | 14 |
| Play the jockey | 15 |
| Play the jester | 15 |
| Play the informer | 17 |
| Play the hostess | 16 |
| Play the host to | 16 |
| Play the horses | 15 |
| Play the highlight reel | 23 |
| Play the high roller | 20 |
| Play the hero | 13 |
| Play the henchman | 17 |
| Play the harp | 13 |
| Play the ham | 12 |
| Play the guitar, say | 20 |
| Play the guitar, in a way | 25 |
| Play the guitar like a guitar god | 33 |
| Play the guitar idly | 20 |
| Play the guitar | 15 |
| Play the goldbricker | 20 |
| Play the gofer | 14 |
| Play the game | 13 |
| Play the fool | 13 |
| Play the flute | 14 |
| Play the first card | 19 |
| Play the firebrand | 18 |
| Play the fink | 13 |
| Play the fife | 13 |
| Play the field, so to speak | 27 |
| Play the entrepreneur | 21 |
| Play the electrician | 20 |
| Play the dulcimer | 17 |
| Play the drone | 14 |
| Play the drama queen | 20 |
| Play the dozens | 15 |
| Play the DJ | 11 |
| Play the dictator | 17 |
| Play the daily double, e.g. | 27 |
| Play the daily double | 21 |
| Play the D.J. | 13 |
| Play the court clown? | 21 |
| Play the coquette | 17 |
| Play the circuit | 16 |
| Play the choice role | 20 |
| Play the Cheshire Cat | 21 |
| Play the card | 13 |
| Play the bully | 14 |
| Play the banjo | 14 |
| Play the balalaika | 18 |
| Play the bagpipes | 17 |
| Play the ace? | 13 |
| Play that won the 1999 Pulitzer for Drama | 41 |
| Play that was the basis for "Cabaret" | 47 |
| Play that the musical "I Do! I Do!" was adapted from | 62 |
| Play that takes place in the afterlife | 38 |
| Play that takes place in an artificial human factory | 52 |
| Play that introduced the word "robot" | 47 |
| Play that introduced the term "robot" | 47 |
| Play that introduced ''robot'' | 46 |
| Play that inspired Puccini | 26 |
| Play that gave us the word "robot" | 44 |
| Play that follows a play | 24 |
| Play that depicts Prince Hal as a mature man | 44 |