| 1966 Grammy winner for "If He Walked Into My Life |
| Emmy winner as Gotti |
| Grammy winner Blige |
| 2000 Best Song Oscar winner |
| Agent noted for Oscar night bashes |
| Australian winner of 11 Grand Slam tournaments |
| A pageant winner's title |
| Academy Award winner with notable eyebrows |
| Five-time Kentucky Derby winner |
| 2018 Best Supporting Actor Oscar nominee Driver |
| 'Arthur' Oscar winner John |
| 'Blue Sky' Oscar winner Jessica |
| Actress Richards who was once married to Charlie Sheen, a role for which I believe she deserves an Oscar |
| A-list screenwriter (and crossword fan) who won an Oscar for "Schindler's List," Steven ___ |
| Les Misérables" Oscar winner Hathaway |
| Actor Jannings, winner of the first Best Actor Oscar |
| 2007 Oscar-nominated teen role for Ellen Page |
| Oscar-winner Witherspoon |
| Golden Globe winner Sedgwick |
| A Fish Called Wanda" Oscar winner |
| Winner of tennis's Grand Slam in 1962 and 1969 |
| 1977 Cy Young Award winner Sparky |
| Oscar for one |
| Academy Award winner Jared who's playing another Joker soon, because lord knows there haven't been enough of those |
| Peace Nobelist Oscar Arias Sanchez, e.g. |
| Dallas Buyers Club" Oscar winner Jared |
| Bee winner's title? |
| Disraeli" Oscar winner, George |
| Winners slangy boast |
| 1966 Grammy winner Eydie |