| TEDDYBOY | Youth of the '50s and '60s wearing Edwardian-style clothes (5,3) |
| TEDDYBOYS | Some U.K. youths of the '50s |
| TED | (Brit) A tough youth of 1950's and 1960's wearing Edwardian style clothes. |
| ATLANTIC | Great independent record label of the 50s and 60s in jazz, rhythm and blues, soul and rock |
| MICROCAR | The King Midget of the '50s and '60s |
| RAMBLERS | AMC cars of the '50s and '60s |
| NYYANKEE | Ford of the '50s and '60s, e.g. |
| BEATNIKS | Counterculturists of the '50s and '60s |
| PAULANKA | He was a teen singing icon in the 50s and 60s, wrote the lyrics for Sinatra's My Way and sang a duet with Lisa Simpson in The Simpsons episode, Treehouse of Horror VI (4,4) |
| FLATIRON | Old-style clothes presser |
| TWIST | Dance craze of the '50s and '60s, The - (5) |
| BENNY | "The Jack ___ Program"; comedy series of the '50s and '60s |
| GIA | British-American actress and model of the '50s and '60s, - Scala (3) |
| CHESSRECORDS | Classic blues label of the '50s and '60s |
| BING | Met manager of the '50s and '60s |
| ABE | Woodson of the '50s and '60s 49ers |
| NERO | Roman emperor of the 50s and 60s |
| IPANA | Toothpaste brand of the 50s and 60s; its mascot was Bucky Beaver (5) |
| RAJ | ___ Kapoor, Bollywood megastar of the 50s and 60s (3) |
| DOUBLEYOURMONEY | TV quiz show of the 50s and 60s hosted by Hughie Green (6,4,5) |