In 1873, the Englishman Joseph Jaggers made the first famous roulette biased wheel attack. Mr. Jaggers with a team of six clerks, clocked all the wheels at the Monte Carlo casino and found one wheel to show significant bias. In their attack exploiting this flaw they won over $325,000, an astronomical sum in 1873.
In the summer of 1891 at the Monte Carlo casino, a part-time swindler and petty crook from London named Charles Wells, broke the bank at each table he played over a period of several days. Breaking the bank meant he won all the available money in the table bank that day, and a black cloth would be placed over the table until the bank was replenished. In song and life he was celebrated as “The Man That Broke the Bank at Monte Carlo.” He later admitted that it was all luck, and he eventually ended up in jail for many years because of his fraudulent schemes.
In the 1942 film Casablanca, Rick’s Café Americain has a trick roulette wheel. The croupier can cause it to land on 22 at will. Rick (Humphrey Bogart) urges a Bulgarian refugee with whose case he becomes sympathetic to put his last three chips on 22 and motions to the croupier to let him win. After the man’s number dramatically comes up, Rick tells him to let it all ride on 22 and lets him win again. Although the details are not mentioned in the film (the croupier only notes that they are “a couple of thousand” down), it appears that Rick has given the man 3885 ((3*36*36)-3) francs.
Near the beginning of the 1973 film The Sting, Johnny Hooker (Robert Redford) takes his share of the money conned from a numbers runner and loses nearly all of it on a single bet against a rigged roulette wheel.
In the third part of the 1998 film Run, Lola, Run, Lola uses all her money to buy a 100-mark chip. (She is actually just short of 100 marks, but gains the sympathy of a casino employee who gives her the chip for what money she has.) She bets her single chip on 20 and wins. She lets her winnings ride on 20 and wins again, making her total winnings 129,600 marks (29,600 more than her smuggler boyfriend owed his boss, Ronnie). The odds of two consecutive wins on the same number on a European roulette wheel are exactly 1369-to-1 against.
In the South Park episode “Red Man’s Greed”, the town, facing destruction at the hands of Native Americans, bets $10,000 to raise money to save themselves. They win, but let it ride, and lose all of it.
In 2004, Ashley Revell of London sold all of his possessions, clothing included, and brought US$135,300 to the Plaza Hotel in Las Vegas and put it all on “Red” at the roulette table in a double-or-nothing bet. The ball landed on “Red 7” and Revell walked away with his net-worth doubled to $270,600.
In the music video for “Palace & Main” by Kent, guitarist Harri Mänty goes to Las Vegas and bets the entire video budget on black. He wins, and the profits were donated to charity.