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1999
Milk Mustache Campaign
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Film
Music
Sports
Television
Other
82.
John Elway
Chris Chandler
Super Bowl XXXIII
Photographer:
Walter Iooss Jr.
83.
John Elway
Super Bowl XXXIII
Photographer:
Walter Iooss Jr.
84.
Stone Cold Steve Austin
Photographer:
Annie Leibovitz
85.
Terrell Davis
Photographer:
Annie Leibovitz
86.
The Cast of
Everybody Loves Raymond
Photographer:
Annie Leibovitz
87.
Whoopi Goldberg
Photographer:
Annie Leibovitz
88.
Mia Hamm
Photographer:
Annie Leibovitz
89.
Jennifer Love Hewitt
Party of Five
Photographer:
Annie Leibovitz
90.
Curly Howard
The Three Stooges
Photographer:
Steve Hellerstein
91.
Peter Criss
Paul Stanley
Ace Frehley
Gene Simmons
KISS
Photographer:
Annie Leibovitz
92.
Hulk
Illustrator:
Adam Kubert
93.
Kermit The Frog
Photographer:
Annie Leibovitz
94.
Billy Quick
Kathy Ireland
Grant Hill
Special Olympics
Photographer:
Walter Iooss Jr.
95.
Bobbi McCaughey
Alexis, Brandon, Joel, Kelsey, Kenny, Natalie & Nathan
Photographer:
Annie Leibovitz
96.
Spider-Man
Illustrator:
Adam Kubert
97.
Nikki McCray
Lisa Leslie
Sheryl Swoopes
Photographer:
Annie Leibovitz
98.
Mike Myers
Austin Powers
Photographer:
Annie Leibovitz
99.
Serena Williams
Venus Williams
Photographer:
Annie Leibovitz
100.
Britney Spears
Photographer:
Annie Leibovitz
101.
Rugrats
Illustration:
Klasky-Csupo
102.
Alex Trebek
Jeopardy
Photographer:
Annie Leibovitz
103.
Tracey Ullman
The Tracey Ullman Show
Photographer:
Annie Leibovitz
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2000