% replaces any number of letters (la% - lake, lamp)_ replaces one letter (ca_ - car, cat)
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The Crossword Solver found 24 answers for The New York Times crossword clue most of 1999 5 letters. The answers have between 3 and 16 letters.

AnswerClue
NINESbetter part of 1999?
MARIAwhen repeated, a 1999 #1 Santana hit
SISQOone-named R&B singer with the 1999 6x platinum album “Unleash the Dragon”
MADRE“Todo Sobre Mi ___” (1999 Almodóvar film)
NINESmost of 1999
DOGMA1999 comedy in which Alanis Morissette plays God
THUMBMADETRICKSsome optical illusions created with one’s fingers [1999]
AGASSIu.S. Open winner of 1994 and 1999
BRENDANfraser of 1999’s “The Mummy”
SHES“___ All That” (1999 rom-com)
NASrapper with the 1999 #1 album “I Am ?”
NEOPETSvirtual critters since 1999
LENcanadian band with the 1999 top 10 hit “Steal My Sunshine”
TCIonetime cable giant acquired by AT&T in 1999
SHES“___ All That” (1999 film)
FEY“S.N.L.” head writer from 1999 to 2006
TLCgirl group with the 1999 #1 album “FanMail”
ARGObest Picture-winning film adapted from the 1999 memoir “The Master of Disguise”
HAMMsoccer star on a 1999 Wheaties box
KIARIOkorean model hitting the scene in 1999
BEEN“Never ___ Kissed” (1999 Drew Barrymore film)
SANTANAband whose 1999 hit “Smooth” spent 12 weeks at #1
JEOPARDYJEOPARDYcrime thriller that takes some liberties with its namesake legal concept (1999)
DOCTORSinternational medical group that won the 1999 Nobel Peace Prize, literally

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