| THISDIAMONDRING | #1 hit by Gary Lewis and the Playboys |
| GIGOLO | Joe from The Journal upsets the lead from Oklahoma and The Playboy (6) |
| OSHEA | Milo of "The Playboys" |
| RAKESIN | Amasses when the playboy's at home (5,2) |
| ORPHANS | 1998 comedy-drama film starring Douglas Henshall and Gary Lewis (7) |
| ELLIOT | Billy ----, Scots actor Gary Lewis played his dad (6) |
| YOUNGGIRL | 1968 song released by Gary Puckett and The Union Gap (5,4) |
| NIL | ___ by Mouth, gritty 1997 film written and directed by Gary Oldman (3) |
| JMSYNGE | Irish playwright whose works include The Playboy of the Western World (1,1,5) |
| TITLEROLE | The main man playing the playboy in The Playboy (5,4) |
| SYNGE | JM, author of the play The Playboy of the Western World (5) |
| GEHRIG | Baseball legend played by Gary Cooper in "The Pride of the Yankees" (1942), Lou ___ |
| GARMIN | Maker of sports watches and GPS technology, founded by Gary Burrell and Min Kao |
| RHODES | Surname shared by Gary, a former TV Chef, and Zandra, the fashion designer (6) |
| SMILE | "When you call me that, ...," said The Virginian, played by Gary Cooper in the 1929 movie |
| MRDEEDS | Role shared by Gary Cooper and Monte Markham |
| DAY | Sports programme presented by Gary Lineker, Match of the --- (3) |
| MATCH | BBC football series hosted by Gary Lineker, ----- of the Day (5) |
| SIRIUS | - - - Black, wizard played by Gary Oldman in the Harry Potter films (6) |
| THEKRAYS | Criminal twins played by Gary and Martin Kemp in 1990 (3,5) |
