Since the dawn of time, man has been a betting animal. Some historical bets have paid off, like sneeze guards at salad bars, while other gambles, such as the mullet, have not.

In a recent post to Reddit’s History community, user HankkMardukas asked, “What are some amazing bets that have been made (and won) in history?”

In response, the history buffs retold the stories of some of the most unlikely wagers ever won.

“You Lose”

Reddit user Timoris shared this West Wing anecdote about President Coolidge winning “The Quiet Game” at a dinner party in the 1920s:

(Hence Coolidge’s nickname, “Silent Cal.”)

Would You Bet Him in a Box?

Did you know one of your favorite children’s books was written on a bet? According to CNN, after Dr. Seuss published The Cat in the Hat (which contains a total of 225 unique words), his editor Bennett Cerf bet him that he couldn’t write a book that used even fewer words.

The doctor of rhymes came back with Green Eggs and Ham, which contains 50.

The Odds Were Slim

Reddit user JohnnyVortex shared the story of Amarillo Slim, a professional poker player who also had a thing for ping pong:

Amarillo Slim at the 2002 World Series of Poker (CryptoDerk/Wikimedia Commons)

According to The New York Times, Slim spent months practicing with both the iron skillet and the glass Coke bottle before placing the bets. That’s dedication.

He also reportedly won $300,000 from Willie Nelson over a game of dominoes by “bet[ting] on which sugar cube a fly would land on.” No idea how he practiced for that one.

Drunken Departure, Ace Arrival

On September 29, 1956, N.J. pilot Thomas Fitzpatrick got drunk in a Uptown Manhattan bar. So, naturally, being a pilot (and being drunk), he bet his barmates that he could fly a plane from N.J. to New York City in 15 minutes—while intoxicated.

At 3 AM on September 30, he stole a plane from the Teterboro Airport, flew back to New York City, and landed perfectly on St. Nicholas Avenue outside the bar.

The best part? Two years later, he did the same thing when a friend at a Washington Heights bar didn’t believe the tale of his first flight. According to the Eugene Register-Guard, when police came after the second street landing, Fitzpatrick denied the deed, but “gave in when he was identified by witnesses.”

Counting Peas

Bill Ebbesen/Wikimedia Commons

Reddit user maclure shared this story, from Weird Universe, of a man named Henry Parish of Meddybemps, Me., who bet his neighbor that he could count one million peas in a month.

The winning prize? $2.50 (and whatever bragging rights come with counting out a million peas).

People in Maine aren’t known for their crazy bets.

Peanut Pusher

Redditor and avid history buff PM_ME_UR_FEET-LADIES shared this tale of a crazy Texan who must have really needed the money:

According to the LA Times, Williams also went through 170 pairs of pants on his three-week peanut-pushing voyage, which set an extremely specific world record.

Call ‘Em the Pittsburgh Gamblers

The 1933 Pittsburgh Pirates, before they were renamed the Steelers in 1940 (via steelersuk.com / Wikimedia Commons)

Redditor TacoSmutKing shared this story of how a simple horse bet helped found a football franchise:

According to the Pittsburgh Post-Gazette, the timeline is a bit off: Rooney founded the football team (originally called the Pirates) in 1933. But the money from his famed 1936 horse bets at Saratoga probably helped the team survive the Great Depression.

Not all redditors found this story heartwarming.

Whatever Gets You Thru the Bet

Live at Madison Square Garden by John Lennon & Elton John (1974)

Redditor Hi-Lander shared the story of a bet between two famous friends: John Lennon and Elton John. According to Keith Badman’s book The Beatles: Off the Record 2, Elton John explains, “We worked on ‘Whatever Gets You Thru the Night‘ and I said, ‘If it reached No. 1, you must play onstage with me.'”

Shortly after its US release on September 23, 1974, the song hit number one on the Billboard charts. Lennon fulfilled his end of the bet on Thanksgiving Day, by joining Elton John on stage at Madison Square Garden as a surprise guest—Lennon’s last major performance.

Upbeatled, indeed.