I've spent over 20 years inside the betting industry. I'll guide you to avoid the hype, ignore the noise, and steer clear of the common pitfalls that catch out everyday punters.
Prop bets have always been the wild west of sports betting Unpredictable, entertaining, and often downright ridiculous. Yet every so often, one of these quirky wagers hits, turning a fun flutter into a story people talk about for years.
From surprise Super Bowl moments to unlikely NFL feats, here are eight prop bets from recent seasons that actually landed.
1. The Super Bowl Marriage Proposal That Made Bettors Smile
Super Bowl LVI (2022) delivered one of the most wholesome prop bet wins in recent memory.
Some betting sites offered odds on whether a player would propose on the field after the game. With “Yes” priced around +400, it felt like wishful thinking.
Then Rams safety Taylor Rapp dropped to one knee after the victory, cashing the bet and creating a fairy-tale moment. Bettors quadrupled their stake, while Rapp walked away with both a ring and a fiancée.
2. The Streaker Who Cashed In On His Own Bet
Super Bowl LV (2021) produced a headline-grabbing payout when a fan bolted onto the field during the fourth quarter. The twist? Florida man Yuri Andrade claimed he had bet on a streaker appearing during the game at +750 odds, and then became the streaker himself to guarantee the outcome.
The stunt reportedly netted him around $370,000 before online betting sites tightened rules to prevent participants from influencing novelty bets. A chaotic moment, a huge payday, and a story still told today.
3. Tears During the National Anthem Turn Into a Winning Wager
Ahead of Super Bowl LVII (2023), one of the more emotional props on the board asked:
“Will a player or coach be shown crying during the national anthem?”
After Eagles coach Nick Sirianni had done exactly that the year before, the “Yes” option was heavily favoured, and it delivered again. Sirianni and several players welled up during Chris Stapleton’s powerful performance, landing the bet comfortably.
A novelty wager that once felt far-fetched has since become a near-expectation at the big game.
4. Jalen Hurts Delivers a Super Bowl ‘Octopus’
An “octopus” is a rare achievement where the same player scores a touchdown and the ensuing two-point conversion, eight points in a row.
Super Bowl LVII (2023) saw Eagles quarterback Jalen Hurts do exactly that, marking the first Super Bowl octopus ever recorded. With odds around 14-to-1, bettors who took a punt on this niche prop were handsomely rewarded.
5. Purple Gatorade Makes a Splash
The post-game Gatorade shower is one of the Super Bowl’s longest-running novelty props, with bettors trying to predict the colour of the celebratory drench.
At Super Bowl LVII (2023), purple, historically a long-shot option at around +800, won big when the Chiefs doused Andy Reid in violet sports drink. The surprise result delighted backers and even sparked a mini-trend: Kansas City used purple again the following year.
6. Every NFL Team Makes a Field Goal on the Same Sunday
One of the most improbable wins came in September 2023, when FanDuel offered a 200-to-1 special requiring every team in the Sunday afternoon slate to make at least one field goal.
It demanded perfection from all 24 teams across 12 games, a feat that had only occurred once in the past two decades. Against the odds, every kicker came through. Over 21,000 bettors shared more than $20 million in winnings, turning a few spare dollars into a collective windfall.
7. 50 Cent’s Surprise Halftime Cameo Hits Long-Shot Odds
Super Bowl LVI’s halftime show (2022) was already star-packed, but a surprise guest stole the betting spotlight. Rapper 50 Cent, not listed as an official performer, suddenly dropped into the set, hanging upside-down in a nod to his iconic “In Da Club” video.
Some bookmakers had included him as an outside possibility in cameo markets, often at around 8-to-1. Those who backed the surprise appearance cashed in nicely.
8. The Early ‘Doink’ That Paid Out Immediately
Many betting sites offer a light-hearted prop on whether any kick in the Super Bowl will hit the uprights or crossbar, affectionately known as a “doink.”
In Super Bowl LVII (2023), bettors didn’t have to wait long. Chiefs kicker Harrison Butker clanged a 42-yard attempt off the left upright in the first quarter, instantly landing all “Yes” bets. The moment was so memorable it even inspired broadcasters to add a special “Doink Cam” for future games.
Final Thoughts
Ridiculous prop bets have produced some of sports betting’s wildest winning moments. Recent standouts include a Super Bowl on-field proposal, a self-made streaker cashing a big wager, Jalen Hurts completing a rare “octopus,” and purple Gatorade landing as a long-shot winner. From emotional national anthem tears to every NFL team making a field goal on the same Sunday, these quirky markets show how unpredictable, and occasionally lucrative, novelty betting can be.
Sources: theweek.com; foxsportsradio.iheart.com; arrowheadaddict.com; reviewjournal.com; people.com; espn.com; cbssports.com;
