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| Season One Picks | ||||||
| Nick | Paul | Josh | Brad | |||
| Entertainers (Screen) | Al Lewis | Elizabeth Taylor | Jerry Lewis | Kirk Douglas | ||
| Entertainers (Screen) | Eddie Albert | Richard Pryor | Karl Maldin | Charlton Heston - Sure Bet | ||
| Entertainers (Screen) | Phillis Diller | Gene Wilder | Jack Palance | Annette Funniciello | ||
| Entertainers (Screen) | Gloria Stuart | James Doohan - Sure Bet | Red Buttons | Christopher Lee | ||
| Entertainers (Screen) | Kitty Carlisle - Sure Bet | Zsa Zsa Gabor | Sid Ceasar | Sherwood Schwartz | ||
| Entertainers (Screen) | Walter Cronkite | Carlo Ponti | Mary-Kate Olsen (u40) | Aaron Spelling | ||
| Entertainers (Music) | Artie Shaw | James Brown | Joey Bishop | BB King | ||
| Entertainers (Music) | Giuseppe Di Stefano | Chuck Berry | Courtney Love | Jimmy Dickens | ||
| Entertainers (Music) | Mary Travers | Dick Clark | George Beverly Shea | Tony Bennett | ||
| Entertainers (Music) | Scott Weiland (u40) | Billy Preston | Andy Griffith | Whitney Houston | ||
| Entertainers (Music) | Bill Cosby | Willie Nelson | Lena Horn | Bobby Brown (u40) | ||
| Entertainers (Music) | Aretha Franklin | Hildegarde | Ozzy Osborne | Etta James | ||
| World Leaders/Politics | Lady Bird Johnson | Boris Yeltsin | William Rehnquist | Gerald Ford | ||
| World Leaders/Politics | Queen Elizabeth | Fidel Castro | Osama Bin Laden | Henry Kissenger | ||
| World Leaders/Politics | Nancy Reagan | Margaret Thatcher | Ted Kennedy | Augusto Pinochet | ||
| World Leaders/Politics | Nelson Mandela | Betty Ford | Bob Dole | Ariel Sharon | ||
| Sports | Stan Musial | Yogi Berra | John Wooden | Eddie Robinson | ||
| Sports | Scott Hamilton | Al Lopez | Muhammed Ali | Bob Feller | ||
| Sports | Willie Mays | Whitey Ford | Red Auerbach | Phil Rizzuto | ||
| Religion | Billy Graham | Gordon Hinkley | Pope JPII - Sure Bet | Abu Musab Al-Zarqawi | ||
| Religion | Clyde Cook | Tammy Faye | Jerry Falwell | Oral Roberts | ||
| Wild Card | Simon Wiesenthal | Rosa Parks | Claude Levi-Strauss | Billy Graham (Wrestler) | ||
| Wild Card | Dalai Llama | Brooke Astor | Stephen Hawking | Estelle Getty | ||
| Wild Card | Ellen Dow | Tara Reid (u40) | Dick Ebersol | Robert Citron | ||
| Couple | J-Lo & Marc Anthony | Nick Cage and his waitress wife | Mr. & Mrs. Kobe Bryant | Usher & Naomi Campbell | ||
| Score | 1 | -1 | 2 | 0 | ||
| "Season One" ends June 16th, 2005 | ||||||