| Life | Hint | Person | % Correct |
|---|---|---|---|
| 1966–2023 | Irish singer with signature song "Nothing Compares 2 U" | Sinead O'Connor | 100%
|
| 1930–2023 | First woman to serve as a U.S. Supreme Court justice | Sandra Day O'Connor | 97%
|
| 1941–2023 | Actor in Love Story and Paper Moon | Ryan O'Neal | 87%
|
| 1972– | 7'1" basketball player who has also acted and rapped | Shaquille O'Neal | 87%
|
| 1963– | Actress in Paper Moon and Bad News Bears | Tatum O'Neal | 87%
|
| Fictional | Protagonist in Gone with the Wind played by Vivien Leigh | Scarlett O'Hara | 82%
|
| 1932–2013 | Starred as Lawrence of Arabia | Peter O'Toole | 82%
|
| 1914–1943 | WW2 fighter ace with an airport named after him | Edward O'Hare | 79%
|
| 1963– | Redheaded late-night talk show host | Conan O'Brien | 76%
|
| 1946– | Family patriarch on Married... with Children and Modern Family | Ed O'Neill | 74%
|
| 1827–1895 | Her cow actually didn't start the Great Chicago Fire. | Catherine O'Leary | 63%
|
| 1954– | Canadian businessman on Shark Tank since 2009 | Kevin O'Leary | 58%
|
| 1970– | Actor in Scent of a Woman and Batman and Robin | Chris O'Donnell | 55%
|
| 1887–1986 | Painter and draftswoman who worked independently | Georgia O'Keeffe | 55%
|
| 1962– | Comedian on The View who also had her own show | Rosie O'Donnell | 55%
|
| 1949– | Conservative political commentator dismissed from Fox News | Bill O'Reilly | 53%
|
| 1975– | Won the World Snooker Championship seven times | Ronnie O'Sullivan | 34%
|