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| Answer | Clue |
|---|
| TYNER | five-time Grammy-winning jazz pianist McCoy ___ |
| ONTO | “___ the Next One,” Grammy-winning Jay-Z song of 2009 |
| MAGNANI | anna ___, first Italian to win an acting Oscar |
| THATSLIFE | “Can’t win ’em all” |
| CROUCHINGTIGER | with an unseen portion of 128-Across, Oscar-winning martial arts film (2000) |
| INIT | still able to win |
| SMARTASS | one clever enough to win every argument ? but not clever enough not to |
| SOLANGE | grammy-winning artist with the 2016 album “A Seat at the Table” |
| LILBABY | grammy-winning rapper with the 2022 #1 album “It’s Only Me” |
| OKFINE | “All right, you win” |
| BADU | grammy-winning Erykah |
| TWENTYONE | card game whose winning hands can be found hidden in 17-, 27-, 42- and 54-Across |
| ENYA | grammy-winning singer who has recorded in several fictional languages |
| RISK | classic board game invented by an Oscar-winning French filmmaker |
| LILA | ___ Kedrova, Oscar-winning actress for “Zorba the Greek” |
| WASH | no-win situation |
| DOERR | pulitzer-winning novelist Anthony |
| TREES | subjects of the 2019 Pulitzer-winning novel “The Overstory” |
| LEACHMAN | cloris ___, Emmy-winning actress on “The Mary Tyler Moore Show” |
| EBERT | first film critic to win a Pulitzer Prize for criticism |
| HOMESTATE | something a presidential candidate often wins |
| DIANA | grammy-winning jazz singer/pianist Krall |
| MAHERSHALAALI | first Muslim actor to win an Academy Award |
| THREEPEAT | winning feat achieved twice by the Green Bay Packers (1929-31, 1965-67) |
| CATE | oscar-winning Blanchett |
| ACETEN | winning blackjack combo |
| ACETEN | winning blackjack hand |
| VIOLA | eGOT-winning actress Davis |
| MORRISON | first Black woman to win the Nobel Prize in Literature |
| KINKYBOOTS | tony Award-winning musical with the song “Sex Is in the Heel” |
| LAHIRI | jhumpa ___, Pulitzer-winning author of “Interpreter of Maladies” |
| GUETTA | david ___, Grammy-winning French D.J. |
| AGEE | pulitzer-winning writer James |
| DANI | “___ California” (Grammy-winning Red Hot Chili Peppers hit) |
| AGEE | pulitzer-winning author who was also a film critic for Time magazine |
| OSAGE | “August: ___ County” (Pulitzer-winning play) |
| ONATEAR | piling up wins |
| MERIT | “Charms strike the sight, but ___ wins the soul”: Alexander Pope |
| ISNT | “Winning ___ everything” |
| ARIANA | grammy-winning Grande |
| ANNE | oscar-winning Hathaway |
| OSLO | 2017 Tony-winning play whose main characters are diplomats |
| AVENUEQ | tony-winning musical with puppets |
| AGEE | pulitzer-winning author whose name is found in nonconsecutive letters of “page turner” |
| NOVA | award-winning PBS docuseries |
| HANA | mandlikova with four Grand Slam tournament wins |
| SPAMALOT | tony-winning musical with the song “Knights of the Round Table” |
| ROMP | easy win |
| RECOUP | win back, as losses |
| GLOAT | win like a loser? |
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