| He originated the line "Bury my heart at Wounded Knee" | 64 |
| He originated the phrase "While there's life, there's hope" | 77 |
| He originates bonds | 19 |
| He ousted Fulgencio | 19 |
| He outlived his twin brother by a few hours | 43 |
| He outmanaged Earl in the 1969 World Series | 43 |
| He outmanaged Sparky in the 1970 World Series | 45 |
| He outpolled H.H.H. in '68 | 30 |
| He outranks a top kick | 22 |
| He outranks a viscount | 22 |
| He outranks the sarge | 21 |
| He overacts | 11 |
| He overthrew Batista | 20 |
| He overthrew Batista in 1959 | 28 |
| He overthrew Bhutto | 19 |
| He overthrew Fulgencio | 22 |
| He overthrew Galba | 18 |
| He overthrew Milton in 1971 | 27 |
| He owes money | 13 |
| He owned "Dem Bums" | 29 |
| He owned a jet named Big Bunny | 30 |
| He owned a rod | 14 |
| He owns an incredible hammer | 28 |
| He packs cotton | 15 |
| He pads parlor pieces | 21 |
| He pained Paine | 15 |
| He painted "Aurora" | 29 |
| He painted "Cape Martin" | 34 |
| He painted "Christina's World" | 44 |
| He painted "Clair de Lune" | 36 |
| He painted "Dog Barking at the Moon" | 46 |
| He painted "Down the Rabbit Hole" | 43 |
| He painted "Haystack at Giverny" | 42 |
| He painted "Interior With Eggplants" | 46 |
| He painted "Launching the Boat" | 41 |
| He painted "Maine Coast" | 34 |
| He painted "Mustache Watch" and "Mustache Hat" | 66 |
| He painted "Old Battersea Bridge" | 43 |
| He painted "Red and White Domes" | 42 |
| He painted "Sens Cathedral" | 37 |
| He painted "The Fife Player" | 38 |
| He painted "The Great Forest" | 39 |
| He painted "The Last Supper" | 38 |
| He painted "The Laughing Cavalier" | 44 |
| He painted "The Life Line" | 36 |
| He painted "The Life-Line" | 36 |
| He painted "The Queen's Party" | 44 |
| He painted "The White Girl" | 37 |
| He painted "Toilers of the Sea" | 41 |
| He painted "Twittering Machine" | 41 |
| He painted a dream world | 24 |
| He painted a fence | 18 |
| He painted a lot of bowlers | 27 |
| He painted G.W. | 15 |
| He painted Hawthorne's portrait | 35 |
| He painted Hawthorne, Wordsworth et al. | 39 |
| He painted Helena Rubinstein | 28 |
| He painted Morisot | 18 |
| He painted scenes of Toledo | 27 |
| He painted the Last Supper surrealistically | 43 |
| He painted Washington | 21 |
| He painted Zola: 1868 | 21 |
| He panicked the U.S. in '38 | 31 |
| He passed Lou in 2009 to become the Yankees' all-time hit leader | 68 |
| He patented the microphone | 26 |
| He paved the hero's way | 27 |
| He pays for the meal | 20 |
| He peddles in public | 20 |
| He peregrinates | 15 |
| He performed 12 labors | 22 |
| He persuaded the Huns not to attack Rome | 40 |
| He pettifogs | 12 |
| He picked Dick | 14 |
| He picked on the Britons | 24 |
| He pined for Beatrice | 21 |
| He pioneered induction motors | 29 |
| He pitched a no-hitter in 1999 | 30 |
| He pitched against Pee Wee | 26 |
| He pitched in the majors at age 59 | 34 |
| He pitched the only World Series perfect game | 45 |
| He pitied the fool | 18 |
| He pities the fool | 18 |
| He pitted Satan vs. Webster | 27 |
| He planned for heavy precipitation | 34 |
| He planted nurseries rather than orchards | 41 |
| He playd Robin | 14 |
| He played "Ponch" | 27 |
| He played "that Tod" in "Parenthood" | 56 |
| He played 007 | 13 |
| He played 2,130 consecutive games | 33 |
| He played a bumpkin named Bodine | 32 |
| He played a cat with no backbone | 32 |
| He played a chauvinistic shoe salesman for ten years | 52 |
| He played a Corleone | 20 |
| He played a gas station attendant on "The Andy Griffith Show" | 71 |
| He played a governor in "Primary Colors" | 50 |
| He played a lion | 16 |
| He played a monocled colonel in a sitcom | 40 |
| He played a Nazi in "Marathon Man" and a Nazi hunter in "The Boys From Brazil" [Connecticut] | 112 |
| He played a sewer worker on TV | 30 |