| 100% | LEOS | 4 | Barack Obama and Lisa Kudrow, for two |
| 44% | LSAT | 4 | Early challenge for Barack and Michelle Obama, for short |
| 42% | DRS | 3 | Jeffrey Kuhlman for Barack Obama and Sean Conley for Donald Trump, for short |
| 40% | ORATOR | 6 | Barack Obama, for one |
| 40% | LEO | 3 | Barack Obama, for one |
| 39% | EXSENATORS | 10 | Obama and Clinton, for example |
| 39% | FEELGOOD | 8 | TV comedy drama with Mae Martin and Lisa Kudrow |
| 39% | NOBEL | 5 | Both Barack Obama and Malala Yousafzai have won one |
| 38% | STATESENATORS | 13 | Barack Obama and Jimmy Carter, at the starts of their political careers |
| 38% | OAHU | 4 | Hawaiian island where Barack Obama and Bruno Mars were born |
| 37% | AMA | 3 | Reddit genre in which Barack Obama and Madonna have participated: Abbr. |
| 37% | AMA | 3 | Reddit genre Barack Obama and Madonna have both participated in (abbr.) |
| 37% | BARTOK | 6 | "Sonata for Two Pianos and Percussion" composer |
| 37% | MEAN | 4 | Two, for one and three? |
| 36% | FRIENDS | 7 | 1994-2004 US television sitcom starring Jennifer Aniston, Courteney Cox and Lisa Kudrow |
| 36% | PAINTINGS | 9 | "Mona Lisa" and "The Starry Night," for two |
| 35% | FACTORS | 7 | Two and one, for two |
| 35% | DEMS | 4 | Barack and Hillary, for ex. |
| 35% | NOBEL | 5 | Prize for Carter and Obama |
| 35% | RACE | 4 | Barack Obama's "Dreams from My Father: A Story of ___ and Inheritance" |
| 35% | NOBELS | 6 | Prizes for Wilson, Carter and Obama |
| 35% | OTTO | 4 | Bus driver for Lisa and Milhouse |
| 35% | OTTO | 4 | Bus driver for Lisa and Bart |
| 35% | TRISECT | 7 | Cut for yourself and two friends |
| 35% | BARRY | 5 | Nickname for Barack Obama |
| 34% | GAMES | 5 | Sorry! and Trouble, for two |
| 34% | LSATS | 5 | Barack, Michelle, Hillary and Bill took them, for short |
| 34% | ADDS | 4 | Puts two and two together, for example |
| 34% | ARETHA | 6 | Inaugural singer for Jimmy, Bill and Barack |
| 34% | OTTO | 4 | Bus driver for Lisa and Bart Simpson |