| Youngest male tennis player to be No. 1 in the ATP Rankings | 59 |
| Youngest NHL player to be inducted into the Hall of Fame | 56 |
| Youngest person to have won an Oscar, Emmy, Tony, and Grammy | 60 |
| Youngest player to be inducted in the Hockey Hall of Fame | 57 |
| Youngest player to be inducted into the Hockey Hall of Fame | 59 |
| Youngest player to join the 500 home run club, familiarly | 57 |
| Youngest player to qualify for an L.P.G.A. Tour event | 53 |
| Youngest player to win a major-league batting title (1955) | 58 |
| Youngest winner in "American Idol" history | 52 |
| Youngster who drinks too much chocolate milk? (homophone) | 57 |
| Your basic "So this guy walks into a bar ..."? | 56 |
| Your grandparents and their friends, snarkily, with "the" | 67 |
| Your one-stop shopping place for on-the-road utensils? | 54 |
| YouTube compilation showing Skywalker's coolest moments? | 60 |
| Yugoslavian-born winner of nine Grand Slam tournaments | 54 |
| Yul Brynner died the same day as ___ Welles (odd fact) | 54 |
| Yum-Yum, Peep-Bo and Pitti-Sing in "The Mikado" | 57 |
| Yvonne with the 1978 #1 hit "If I Can't Have You" | 63 |