Season 5

Cynthia Nixon

January 4, 2000

Robbie Williams

January 5, 2000

Richard Belzer

January 6, 2000

Joe Montana

January 10, 2000

Will Ferrell

January 11, 2000

Ice Cube

January 12, 2000

Michael Stipe

January 13, 2000

Penelope Ann Miller

January 17, 2000

Frankie Muniz

January 18, 2000

Freddie Prinze Jr.

January 19, 2000

Jerry Springer

January 20, 2000

Selma Blair

January 24, 2000

Peter Krause

January 25, 2000

Jenny McCarthy

January 26, 2000

David Arquette

January 27, 2000

Jeff Bridges

February 1, 2000

Bob Dole

February 2, 2000

Jason Priestly

February 3, 2000

Moby

February 14, 2000

Dennis Farina

February 15, 2000

Matthew Perry

February 16, 2000

Ed McMahon

February 17, 2000

Snoop Dogg

February 22, 2000

Charlize Theron

February 23, 2000

Rachael Leigh Cook

February 24, 2000

Forest Whitaker

February 28, 2000

Vin Diesel

February 29, 2000

Tobey Maguire

March 1, 2000

Ellen DeGeneres

March 2, 2000

Neil Patrick Harris

March 6, 2000

Kevin Pollak

March 7, 2000

Bob Dole

March 8, 2000

Garry Shandling

March 9, 2000

Eddie Izzard

March 13, 2000

Kim Delaney

March 14, 2000

Wolf Blitzer

March 15, 2000

Drew Carey

March 16, 2000

Chris Meloni

March 20, 2000

Marla Sokoloff

March 21, 2000

Eric Idle

March 22, 2000

Leelee Sobieski

March 23, 2000

John Lydon

March 27, 2000

Joshua Jackson

March 28, 2000

Triumph the Insult Comic Dog

March 29, 2000

Jimmy Smits

March 30, 2000

Roger Daltrey

April 10, 2000

Ben Stein

April 11, 2000

Patrick Stewart

April 12, 2000

David Alan Grier

April 13, 2000

Stanley Tucci

April 17, 2000

Samantha Mathis

April 18, 2000

Diamond Dallas Page

April 19, 2000

Arlen Specter

April 20, 2000

Hugh Hefner

April 24, 2000

Kirsten Dunst

April 25, 2000

Jeanne Tripplehorn

April 26, 2000

Stephen Baldwin

April 27, 2000

S. Epatha Merkerson

May 1, 2000

Luke Wilson

May 2, 2000

Julie Warner

May 3, 2000

Eric Close

May 4, 2000

Wendie Malick

May 8, 2000

Jesse L. Martin

May 9, 2000

Andy Richter

May 10, 2000

Betty White

May 11, 2000

Tracey Ullman

May 15, 2000

Kyle MacLachlan

May 16, 2000

Jane Leeves

May 17, 2000

Michael Rapaport

May 18, 2000

Thandie Newton

May 29, 2000

Laura Kightlinger

May 30, 2000

Sonja Christopher

May 31, 2000

Penn and Teller

June 5, 2000

Kelli Williams

June 6, 2000

Michael Moore

June 7, 2000

When the Elderly Go on TV with Al Greenwood

June 12, 2000

Mark Curry

June 13, 2000

Jimmy Kimmel & Adam Carolla

June 14, 2000

Julie Brown

June 15, 2000

Heather Donahue

June 19, 2000

Joe Lockhart

June 20, 2000

Freddie Prinze Jr.

June 21, 2000

Alicia Silverstone

June 22, 2000

Cheri Oteri

June 26, 2000

Jeff Probst

June 27, 2000

Richie Sambora

June 28, 2000

John C. Reilly

June 29, 2000

Anna Paquin

July 10, 2000

J.K. Simmons

July 11, 2000

Famke Janssen

July 12, 2000

Billy Crudup

July 13, 2000

Shawn & Marlon Wayans

July 17, 2000

Halle Berry

July 18, 2000

Fourth Anniversary Special

July 19, 2000

Al Roker

July 20, 2000

Peter Fonda

July 24, 2000

Joe Eszterhas

July 25, 2000

Jennifer Beals

July 26, 2000

Campaign Trail to the Road to the White House

July 31, 2000

Republican National Convention Pt. 1

August 1, 2000

Republican National Convention Pt. 2

August 2, 2000

Republican National Convention Pt. 3

August 3, 2000

Republican National Convention Pt. 4

August 4, 2000

Democratic National Convention Pt. 1

August 15, 2000

Democratic National Convention Pt. 2

August 16, 2000

Democratic National Convention Pt. 3

August 17, 2000

Democratic National Convention Pt. 4

August 18, 2000

Jeremy Piven

August 22, 2000

Slash

August 23, 2000

Vincent D'Onofrio

August 24, 2000

Donal Logue

September 5, 2000

Greg Kinnear

September 6, 2000

Spinal Tap

September 7, 2000

Joe Mantegna

September 11, 2000

Eugene Levy

September 12, 2000

Lennox Lewis

September 13, 2000

Senator Joe Lieberman

September 14, 2000

Ryan Phillippe

September 18, 2000

Jamie Lee Curtis

September 19, 2000

Barenaked Ladies

September 20, 2000

Jamie Foxx

September 21, 2000

Jonathan Katz

September 25, 2000

Bill Goldberg

September 26, 2000

Sylvester Stallone

September 27, 2000

Tony Danza

September 28, 2000

Dean Cain

October 2, 2000

Ashton Kutcher

October 3, 2000

Jewel

October 4, 2000

Ralph Nader

October 5, 2000

Alice Cooper

October 16, 2000

Christian Slater

October 17, 2000

Joshua Jackson

October 18, 2000

Brendan Fraser

October 19, 2000

Kevin James

October 23, 2000

Jeff Garlin

October 24, 2000

Posh Spice & Baby Spice

October 25, 2000

Steven Weber

October 26, 2000

Brett Butler

October 30, 2000

David Frost

October 31, 2000

Phil Donahue

November 1, 2000

Michael Richards

November 2, 2000

Arlen Specter

November 6, 2000

Indecision 2000 Choose and Loose

November 7, 2000

Richard Belzer

November 8, 2000

Michael Moore

November 9, 2000

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

Adam Sandler

November 13, 2000

Patricia Arquette

November 14, 2000

Adam Sandler

November 15, 2000

Rhys Ifans

November 16, 2000

Tales of Survival with Vance DeGeneres

November 20, 2000

John Goodman

November 27, 2000

Laura San Giacomo

November 28, 2000

Billy Campbell

November 29, 2000

Anthony Clark

November 30, 2000

Thomas Gibson

December 4, 2000

Faith Ford

December 5, 2000

Chris O'Donnell

December 6, 2000

Marlan Wayans

December 7, 2000

Ira Glass

December 11, 2000

Greta Van Susteren

December 12, 2000

Indecision 2000 Special

December 13, 2000

Wolf Blitzer

December 14, 2000

Marla Sokoloff

December 18, 2000

Marisa Tomei

December 19, 2000

Jeri Ryan

December 20, 2000

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

Gillian Anderson

December 21, 2000

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