January 4, 2000

Season 5

01. Cynthia Nixon

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January 4, 2000

02. Robbie Williams

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January 5, 2000

03. Richard Belzer

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January 6, 2000

04. Joe Montana

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January 10, 2000

05. Will Ferrell

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January 11, 2000

06. Ice Cube

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January 12, 2000

07. Michael Stipe

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January 13, 2000

08. Penelope Ann Miller

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January 17, 2000

09. Frankie Muniz

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January 18, 2000

10. Freddie Prinze Jr.

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January 19, 2000

11. Jerry Springer

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January 20, 2000

12. Selma Blair

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January 24, 2000

13. Peter Krause

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January 25, 2000

14. Jenny McCarthy

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January 26, 2000

15. David Arquette

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January 27, 2000

16. Jeff Bridges

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February 1, 2000

17. Bob Dole

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February 2, 2000

18. Jason Priestly

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February 3, 2000

19. Moby

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February 14, 2000

20. Dennis Farina

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February 15, 2000

21. Matthew Perry

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February 16, 2000

22. Ed McMahon

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February 17, 2000

23. Snoop Dogg

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February 22, 2000

24. Charlize Theron

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February 23, 2000

25. Rachael Leigh Cook

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February 24, 2000

26. Forest Whitaker

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February 28, 2000

27. Vin Diesel

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February 29, 2000

28. Tobey Maguire

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March 1, 2000

29. Ellen DeGeneres

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March 2, 2000

30. Neil Patrick Harris

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March 6, 2000

31. Kevin Pollak

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March 7, 2000

32. Bob Dole

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March 8, 2000

33. Garry Shandling

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March 9, 2000

34. Eddie Izzard

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March 13, 2000

35. Kim Delaney

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March 14, 2000

36. Wolf Blitzer

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March 15, 2000

37. Drew Carey

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March 16, 2000

38. Chris Meloni

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March 20, 2000

39. Marla Sokoloff

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March 21, 2000

40. Eric Idle

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March 22, 2000

41. Leelee Sobieski

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March 23, 2000

42. John Lydon

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March 27, 2000

43. Joshua Jackson

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March 28, 2000

44. Triumph the Insult Comic Dog

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March 29, 2000

45. Jimmy Smits

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March 30, 2000

46. Roger Daltrey

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April 10, 2000

47. Ben Stein

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April 11, 2000

48. Patrick Stewart

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April 12, 2000

49. David Alan Grier

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April 13, 2000

50. Stanley Tucci

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April 17, 2000

51. Samantha Mathis

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April 18, 2000

52. Diamond Dallas Page

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April 19, 2000

53. Arlen Specter

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April 20, 2000

54. Hugh Hefner

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April 24, 2000

55. Kirsten Dunst

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April 25, 2000

56. Jeanne Tripplehorn

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April 26, 2000

57. Stephen Baldwin

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April 27, 2000

58. S. Epatha Merkerson

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May 1, 2000

59. Luke Wilson

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May 2, 2000

60. Julie Warner

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May 3, 2000

61. Eric Close

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May 4, 2000

62. Wendie Malick

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May 8, 2000

63. Jesse L. Martin

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May 9, 2000

64. Andy Richter

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May 10, 2000

65. Betty White

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May 11, 2000

66. Tracey Ullman

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May 15, 2000

67. Kyle MacLachlan

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May 16, 2000

68. Jane Leeves

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May 17, 2000

69. Michael Rapaport

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May 18, 2000

70. Thandie Newton

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May 29, 2000

71. Laura Kightlinger

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May 30, 2000

72. Sonja Christopher

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May 31, 2000

73. Penn and Teller

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June 5, 2000

74. Kelli Williams

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June 6, 2000

75. Michael Moore

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June 7, 2000

76. When the Elderly Go on TV with Al Greenwood

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June 12, 2000

77. Mark Curry

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June 13, 2000

78. Jimmy Kimmel & Adam Carolla

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June 14, 2000

79. Julie Brown

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June 15, 2000

80. Heather Donahue

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June 19, 2000

81. Joe Lockhart

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June 20, 2000

82. Freddie Prinze Jr.

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June 21, 2000

83. Alicia Silverstone

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June 22, 2000

84. Cheri Oteri

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June 26, 2000

85. Jeff Probst

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June 27, 2000

86. Richie Sambora

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June 28, 2000

87. John C. Reilly

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June 29, 2000

88. Anna Paquin

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July 10, 2000

89. J.K. Simmons

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July 11, 2000

90. Famke Janssen

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July 12, 2000

91. Billy Crudup

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July 13, 2000

92. Shawn & Marlon Wayans

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July 17, 2000

93. Halle Berry

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July 18, 2000

94. Fourth Anniversary Special

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July 19, 2000

95. Al Roker

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July 20, 2000

96. Peter Fonda

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July 24, 2000

97. Joe Eszterhas

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July 25, 2000

98. Jennifer Beals

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July 26, 2000

99. Campaign Trail to the Road to the White House

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July 31, 2000

100. Republican National Convention Pt. 1

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August 1, 2000

101. Republican National Convention Pt. 2

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August 2, 2000

102. Republican National Convention Pt. 3

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August 3, 2000

103. Republican National Convention Pt. 4

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August 4, 2000

104. Democratic National Convention Pt. 1

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August 15, 2000

105. Democratic National Convention Pt. 2

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August 16, 2000

106. Democratic National Convention Pt. 3

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August 17, 2000

107. Democratic National Convention Pt. 4

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August 18, 2000

108. Jeremy Piven

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August 22, 2000

109. Slash

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August 23, 2000

110. Vincent D'Onofrio

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August 24, 2000

111. Donal Logue

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September 5, 2000

112. Greg Kinnear

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September 6, 2000

113. Spinal Tap

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September 7, 2000

114. Joe Mantegna

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September 11, 2000

115. Eugene Levy

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September 12, 2000

116. Lennox Lewis

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September 13, 2000

117. Senator Joe Lieberman

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September 14, 2000

118. Ryan Phillippe

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September 18, 2000

119. Jamie Lee Curtis

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September 19, 2000

120. Barenaked Ladies

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September 20, 2000

121. Jamie Foxx

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September 21, 2000

122. Jonathan Katz

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September 25, 2000

123. Bill Goldberg

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September 26, 2000

124. Sylvester Stallone

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September 27, 2000

125. Tony Danza

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September 28, 2000

126. Dean Cain

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October 2, 2000

127. Ashton Kutcher

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October 3, 2000

128. Jewel

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October 4, 2000

129. Ralph Nader

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October 5, 2000

130. Alice Cooper

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October 16, 2000

131. Christian Slater

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October 17, 2000

132. Joshua Jackson

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October 18, 2000

133. Brendan Fraser

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October 19, 2000

134. Kevin James

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October 23, 2000

135. Jeff Garlin

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October 24, 2000

136. Posh Spice & Baby Spice

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October 25, 2000

137. Steven Weber

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October 26, 2000

138. Brett Butler

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October 30, 2000

139. David Frost

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October 31, 2000

140. Phil Donahue

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November 1, 2000

141. Michael Richards

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November 2, 2000

142. Arlen Specter

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November 6, 2000

143. Indecision 2000 Choose and Loose

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November 7, 2000

144. Richard Belzer

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November 8, 2000

145. Michael Moore

Tonight, documentary director Michael Moore promoting his TV series on Bravo called The Awful Truth.

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November 9, 2000

146. Adam Sandler

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November 13, 2000

147. Patricia Arquette

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November 14, 2000

148. Adam Sandler

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November 15, 2000

149. Rhys Ifans

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November 16, 2000

150. Tales of Survival with Vance DeGeneres

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November 20, 2000

151. John Goodman

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November 27, 2000

152. Laura San Giacomo

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November 28, 2000

153. Billy Campbell

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November 29, 2000

154. Anthony Clark

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November 30, 2000

155. Thomas Gibson

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December 4, 2000

156. Faith Ford

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December 5, 2000

157. Chris O'Donnell

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December 6, 2000

158. Marlan Wayans

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December 7, 2000

159. Ira Glass

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December 11, 2000

160. Greta Van Susteren

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December 12, 2000

161. Indecision 2000 Special

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December 13, 2000

162. Wolf Blitzer

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December 14, 2000

163. Marla Sokoloff

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December 18, 2000

164. Marisa Tomei

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December 19, 2000

165. Jeri Ryan

Tonight, actress Jeri Ryan promotes her new movie Dracula 2000.

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December 20, 2000

166. Gillian Anderson

Tonight, actress Gillian Anderson from the The X-Files.

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December 21, 2000