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  • Any time a contestant goes for it all in "Beat the Dealer", and picks either the highest possible number for themselves or the lowest possible number for Monty/Wayne.
  • Anybody who won the Super Deal in either era.
  • The last episode of the 1971-77 syndicated run, and by extension the "classic" 1963-77 era. Besides there not being a Zonk in sight (specifically, at no point was there a Zonk even present during the whole show; everybody was guaranteed to win something), it ended with a Big Deal win.
    • On a more fun note, the show started with Monty's daughter and son-in-law, Joanna and Paul Gleason.
  • In the original version, it wasn't unheard of for enough traders to decline going for the Big Deal that Monty would eventually start asking Zonked contestants to compete for it (remember, the original rules allowed for two separate traders to play). Any contestant who went from being Zonked to winning the Big Deal would definitely qualify.
  • In the Wayne Brady revival version, during Monty Hall Week in 2010 (where Hall returned to do one deal a day for a week), Monty's deal on March 24 was the updated version of "Monty's Cash Register", the "Cash Board". In the game, a couple is given a board with 15 cards — 13 are dollar amounts, two are Zonks. The object for the couple is to keep turning cards until they collect $1000 of the available $1800, at which point they also win a car — as long as they don't hit the Zonk first. On this playing, the couple turned over the Zonk with their first card. Monty, pretending to call an audible (but using the consolation rule from the old Cash Register game), told the couple that they could turn another card. If it was cash, he'd double it. If it was the other Zonk, they got the car. Of course, since this is on the Awesome page, you know what happened next.
    • This feat was repeated on December 8, 2016, prompting Wayne to say that this was only the second time this had ever happened.
  • On October 24th, 2012, a contestant played a game called "The Great Escape" to win a car. The object of the game is to find the one key in a set of 15 that will unlock a glass box containing the car keys, within a time limit. You get 15 seconds at the outset and $1,500 cash, and you can buy extra time at $100 per second. This contestant found the winning key on her very first try, something that had never happened on the show up to that point.
    • It happened again less than a month later, on the November 20th show, when an entire family was called up to play.
    • It happened a third time on the Jan. 30th, 2013 "Twitter" episode, when the game for the contestant to play was chosen beforehand by voters online.
    • January 22, 2024: Contestant Sonya plays The Great Escape for a trip to Costa Rica worth over $ 9,300. She gives up $1000 of her money to gain an additional ten seconds but the very first key she picks winds up being the one to unlock the box with the plane tickets!
  • The occasions where a contestant gives up a car for the Big Deal and wins it. So far it's happened six times on the Brady version - once for $23,002, the other five times for another car.
  • For the week of May 6-10. 2013, Publisher's Clearing House offered $20,000 per day in one of the show's deals. Every single day, someone won the 20K, including the show's first ever win in "Smash For Cash" on Monday's show.
  • On June 7, 2013, a contestant playing Car Pong not only gets the ball in the CAR cup on his first throw, he gets a second ball in the cup! Sadly, the player was only eligible for one car.
  • During the week of June 17, 2013, a contestant has a chance to win a car (of course, she doesn't know it yet). She passes up a chance to look behind the curtain to keep an envelope Wayne has given her. The car is revealed. She passes up a chance to take the prize in the small box, choosing again to keep the envelope. Turns out, it was a second chance at the car. He then offers her the Big Box. This time, she gives up the envelope, which contains a zonk. What's in the Big Box? Yep.
  • This is Wayne's first steady TV job since taping for the first American run of Whose Line Is It Anyway? ended in 2003.
  • One of the games played during the 2015 April Fools episode was Plinko.
  • On the December 20, 2017 episode, a new rule was in effect for the Big Deal in which one of the doors had an envelope attached to it containing a bonus prize. This led to a very memorable Bait-and-Switch; the contestant (who was the top winner with accessories) was steered towards Door #2 with the aforementioned envelope. Behind the door was a spa, which did not seem like the Big Deal ... until Wayne opened the envelope, which contained $15,000!
  • On April 23, 2020, a contestant was unable to gain extra time for Car Pong beyond the default 5 seconds. She gets the ball in the CAR cup, against all odds, prompting Wayne to tell viewers at home that they can do it too.
  • Any time a player pulls a reverse Zonk or "Does The Monty". What that means is during "Monty's Cash Register" if they get zonked on the first turn, they get offered the chance to get the car if they find the second zonk.
  • February 5, 2024, dealer Kelly won $ 15,000, a home theatre and a trip to San Diego while playing Race to the Finish, and only picked one spade.

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