Playboy Interview Subjects [2000s]

Sexiest Playboy

Listing of a TV program indicates a joint interview of the cast. Missing: Rowland Evans (2001)

This Category is Ranked. Sort by Ranking Based on Votes by clicking on Vote Ranking. Sort by the Collection's Ranking by clicking on List Ranking.

Vote RankingList Ranking  

1

2000

Hugh Hefner

Publisher

100% (2 of 2 votes)

25

2000

Ben Stiller

Actor

71.43% (15 of 21 votes)

41

2000

Drew Barrymore

Actress

55.56% (5 of 9 votes)

43

2000

Jon Stewart

Comedian

54.55% (6 of 11 votes)

44

2000

Bob Costas

Sportscaster

54.48% (79 of 145 votes)

52

2000

Jeff Bezos

Entrepreneur

50.0% (9 of 18 votes)

53

2000

Pete Rose

Baseball Player

50.0% (11 of 22 votes)

54

2000

George Clooney

Actor

50.0% (16 of 32 votes)

70

2000

Trey Parker

Animator

42.86% (3 of 7 votes)

71

2000

Matt Stone

Animator

42.86% (3 of 7 votes)

78

2000

Jennifer Lopez

Vocalist

12.37% (58 of 469 votes)

79

2000

Robert Novak

Commentator

0% (0 of 0 votes)

80

2000

John Malkovich

Actor

0% (0 of 0 votes)

2

2001

Bobby Knight

Basketball Coach

100% (2 of 2 votes)

3

2001

Tom Green

Comedian

100% (1 of 1 votes)

27

2001

Will Smith

Vocalist

69.41% (295 of 425 votes)

37

2001

Chris Matthews

Commentator

60.98% (25 of 41 votes)

42

2001

Gary Johnson

U.S. Governor

54.55% (6 of 11 votes)

56

2001

Charlie Sheen

Actor

50.0% (2 of 4 votes)

76

2001

Metallica

Musicians

16.67% (2 of 12 votes)

81

2001

Vince McMahon

Wrestler

0% (0 of 0 votes)

84

2001

West Wing

TV Series

0% (0 of 0 votes)

85

2001

Tim Burton

Filmmaker

0% (0 of 0 votes)

86

2001

Coen Brothers

Filmmaker

0% (0 of 1 votes)

4

2002

Brit Hume

Commentator

100% (1 of 1 votes)

5

2002

Allen Iverson

Basketball Player

100% (1 of 1 votes)

34

2002

Denzel Washington

Actor

63.64% (35 of 55 votes)

36

2002

Al Michaels

Sportscaster

61.80% (55 of 89 votes)

55

2002

Fred Durst

Vocalist

50.0% (5 of 10 votes)

69

2002

Willie Nelson

Vocalist

42.86% (3 of 7 votes)

74

2002

Bill O'Reilly

Commentator

28.57% (2 of 7 votes)

82

2002

Harrison Ford

Actor

0% (0 of 0 votes)

83

2002

Larry Ellison

Entrepreneur

0% (0 of 0 votes)

87

2002

Lennox Lewis

Boxer

0% (0 of 0 votes)

88

2002

Curt Schilling

Baseball Player

0% (0 of 0 votes)

89

2002

Gary Hart

U.S. Senator

0% (0 of 0 votes)

6

2003

Billy Bob Thornton

Actor

100% (1 of 1 votes)

7

2003

Tobey Maguire

Actor

100% (1 of 1 votes)

8

2003

Quentin Tarantino

Filmmaker

100% (3 of 3 votes)

38

2003

Jimmy Kimmel

TV Personality

59.46% (66 of 111 votes)

40

2003

Halle Berry

Actress

56.06% (37 of 66 votes)

47

2003

Colin Farrell

Actor

50.0% (1 of 2 votes)

48

2003

Jay-Z

Vocalist

50.0% (1 of 2 votes)

49

2003

John Cusack

Actor

50.0% (4 of 8 votes)

50

2003

Jon Gruden

Football Coach

50.0% (13 of 26 votes)

64

2003

O.J. Simpson

Football Player

47.81% (109 of 228 votes)

66

2003

Lisa Marie Presley

Vocalist

45.48% (287 of 631 votes)

9

2004

Jack Nicholson

Actor

100% (1 of 1 votes)

10

2004

Oliver Stone

Filmmaker

100% (2 of 2 votes)

21

2004

Johnny Depp

Actor

87.50% (14 of 16 votes)

24

2004

Donald Trump

U.S. President

73.43% (1683 of 2292 votes)

28

2004

Bernie Mac

Comedian

68.75% (11 of 16 votes)

51

2004

Derek Jeter

Baseball Player

50.0% (10 of 20 votes)

72

2004

Jim Carrey (Comedian)

Comedian

37.50% (3 of 8 votes)

73

2004

Matt Damon

Actor

33.33% (1 of 3 votes)

77

2004

Michael Moore

Filmmaker

14.08% (10 of 71 votes)

90

2004

Kiefer Sutherland

Actor

0% (0 of 0 votes)

91

2004

50 Cent

Vocalist

0% (0 of 0 votes)

92

2004

Sergey Brin

Computer Tech

0% (0 of 1 votes)

93

2004

Larry Page

Computer Tech

0% (0 of 0 votes)

11

2005

Pierce Brosnan

Actor

100% (1 of 1 votes)

20

2005

Jamie Foxx

Comedian

95.24% (20 of 21 votes)

23

2005

Owen Wilson

Actor

75.00% (15 of 20 votes)

32

2005

Rock (Dwayne Johnson)

Wrestler

65.32% (81 of 124 votes)

45

2005

Nicole Kidman

Actress

53.85% (7 of 13 votes)

46

2005

Toby Keith

Vocalist

50.0% (1 of 2 votes)

67

2005

George Carlin

Comedian

45.45% (5 of 11 votes)

94

2005

Les Moonves

Entrepreneur

0% (0 of 0 votes)

95

2005

Thomas Friedman

Commentator

0% (0 of 0 votes)

96

2005

James Spader

Actor

0% (0 of 0 votes)

97

2005

Lance Armstrong

Athlete

0% (0 of 0 votes)

98

2005

Ewan McGregor

Actor

0% (0 of 0 votes)

12

2006

Mark Cuban

Sports Executive

100% (1 of 1 votes)

29

2006

Kanye West

Vocalist

68.54% (122 of 178 votes)

35

2006

Al Franken

Comedian

61.90% (26 of 42 votes)

61

2006

Ludacris

Vocalist

50.0% (2 of 4 votes)

62

2006

Dixie Chicks

Vocalists

50.0% (1 of 2 votes)

68

2006

Keanu Reeves

Actor

43.56% (159 of 365 votes)

109

2006

Ozzie Guillen

Baseball Player

0% (0 of 0 votes)

110

2006

Shepard Smith

Commentator

0% (0 of 0 votes)

111

2006

Michael Brown (FEMA)

Bureaucrat

0% (0 of 0 votes)

112

2006

Jerry Bruckheimer

Entrepreneur

0% (0 of 0 votes)

113

2006

Denis Leary

Comedian

0% (0 of 1 votes)

114

2006

Arianna Huffington

Commentator

0% (0 of 0 votes)

13

2007

Steve Nash

Basketball Player

100% (1 of 1 votes)

14

2007

Chris Tucker

Actor

100% (5 of 5 votes)

30

2007

Bill Maher

Comedian

66.67% (2 of 3 votes)

33

2007

Simon Cowell

TV Personality

64.29% (18 of 28 votes)

59

2007

Keith Olbermann

Sportscaster

50.0% (25 of 50 votes)

60

2007

Bruce Willis

Actor

50.0% (1 of 2 votes)

102

2007

Clive Owen

Actor

0% (0 of 0 votes)

103

2007

Robert Redford

Actor

0% (0 of 0 votes)

104

2007

Bill Richardson

U.S. Governor

0% (0 of 0 votes)

115

2007

T. Boone Pickens

Entrepreneur

0% (0 of 0 votes)

116

2007

Jeremy Piven

Actor

0% (0 of 0 votes)

117

2007

Matt Groening

Animator

0% (0 of 0 votes)

19

2008

Steve Carell

Comedian

98.25% (56 of 57 votes)

22

2008

Drew Pinsky

Doctor

78.57% (22 of 28 votes)

26

2008

Ben Stiller

Actor

71.43% (15 of 21 votes)

31

2008

Pete Wentz

Musician

66.67% (2 of 3 votes)

58

2008

Dana White

Entrepreneur

50.0% (5 of 10 votes)

65

2008

Tina Fey

Comedienne

47.28% (113 of 239 votes)

75

2008

Matthew McConaughey

Actor

20.0% (1 of 5 votes)

99

2008

Garry Kasparov

Chess Champ

0% (0 of 0 votes)

100

2008

Chad Kroeger

Musician

0% (0 of 0 votes)

101

2008

Fareed Zakaria

Commentator

0% (0 of 0 votes)

105

2008

Daniel Craig

Actor

0% (0 of 0 votes)

106

2008

Hugh Jackman

Actor

0% (0 of 0 votes)

15

2009

Kenny Chesney

Vocalist

100% (1 of 1 votes)

16

2009

Chuck Palahniuk

Author

100% (1 of 1 votes)

17

2009

Shia LaBeouf

Actor

100% (6 of 6 votes)

18

2009

Seth MacFarlane

Animator

100% (1 of 1 votes)

39

2009

James Cameron

Filmmaker

58.64% (173 of 295 votes)

57

2009

Woody Harrelson

Actor

50.0% (1 of 2 votes)

63

2009

Alec Baldwin

Actor

48.21% (27 of 56 votes)

107

2009

Richard Branson

Entrepreneur

0% (0 of 0 votes)

108

2009

Hugh Laurie

Comedian

0% (0 of 1 votes)

118

2009

Seth Rogen

Actor

0% (0 of 0 votes)

119

2009

Benicio Del Toro

Actor

0% (0 of 1 votes)