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written by Sam Greenspan

For the 14th year in a row, I bet real money on crazy Super Bowl bets including Macaulay Culkin, crypto shoutouts, the Ickey Shuffle, and halftime sunglasses.

Welcome to year 14!

During the Super Bowl, sportsbooks around the world — primarily in small island countries without laws — offer tons of ridiculous bets. The bets generally have terrible odds, which is why, 14 years in, I remain the only writer self-destructive enough to put actual money on these bets.

I took it on the chin last year, with my worst showing ever; I went 3-7-1 on my bets and lost $52.57. That brings my lifetime total to -$161.68 after nearly one-and-a-half decades of making Super Bowl prop bets. Not great.

So this year, I’m here for redemption. And I might have a shot. Two of the bests I lose every year (the Puppy Bowl and the first song performed during halftime) are out. New bets are in. Even a few where (what I believe to be) the obvious pick has player-friendly odds.

Here are 11 strange prop bets, all of which I actually made.

1 | How long will it take Mickey Guyton to sing the National Anthem?

Over 1:40 -135
Under 1:40 +105

Step one: Figure out who Mickey Guyton is. (This is no indictment of Mickey Guyton and/or her fame, by the way, it’s entirely an indictment of me diving headfirst into the “40-year-old parent of small children” stereotype where I only listen to either music from my youth or kids songs. Storybots actually has some decent music.)

Step two: Now that I’ve done that, time to see if I can find a prior example of her singing the National Anthem. Here’s one from a PBS Memorial Day concert in 2021 which checks in at a breezy 1:23. Here’s another one from a country music radio event from 2015 that’s only slightly longer.

So now I’m shook. It’s always been my policy to bet the over on the National Anthem and that bet usually serves me well. But both of Mickey Guyton’s prior performances are significantly shorter than the over-under bar. So I’m actually going to break my policy and bet the under.

I bet $11 on UNDER 1:40 to win $11.55 (total payout $22.55)

2 | Will Joe Burrow be compared to Macaulay Culkin?

No -2000
Yes +700

I assume the sportsbook means Joe Burrow will be compared to Macaulay Culkin by someone on the broadcast and not, you know, by anyone in life.

While I know it feels like throwing $11 into the garbage, I’ve got to go with “Yes.” I can’t bet “no” at -2000, not when I need to climb out of a hole. My hope: Either Macaulay Culkin is shown in the stands if the broadcast features a “we’re in L.A., look at all these celebrities in the crowd” montage… or the broadcast does a “we’re in L.A., let’s compare these Super Bowl players to movie stars” montage. That’s so much faith in montages.

I bet $11 on YES to win $77 (total payout $88.00)

3 | What will be shown first during the game?

Hollywood Sign -300
Hollywood Walk of Fame +200

Back when the Super Bowl was in San Francisco-adjacent in 2018, I bet that the Golden Gate Bridge would not be shown during the broadcast. This was a bad call. I noted in my review of my bets:

“I really had no memory of the Super Bowl broadcast including local footage coming in and out of commercial; I thought they’d only show overhead shots of the stadium. Turns out they show a ton of the stuff, and even though Santa Clara isn’t San Francisco, the Golden Gate bridge made multiple appearances.”

Which brings us to now. While the Super Bowl is down in Inglewood, we’re going to get some Los Angeles B-roll in and out (not In & Out) of commercials, and that’s going to include the Hollywood landmarks. As much as I’d like to bet on the Walk of Fame at positive odds, it’s gotta be the Hollywood Sign. The Walk of Fame doesn’t have one singular spot to focus on like the Hollywood Sign. Frankly, it would’ve been a harder choice between the Hollywood Sign, that Santa Monica pier sign, and a classic overhead shot of freeway traffic.

I bet $11 on HOLLYWOOD SIGN to win $3.67 (total payout $14.67)

4 | Will a player do the Ickey Shuffle?

Yes -140
No +100

With the Cincinnati Bengals in the Super Bowl, everyone’s thinking about former Bengals player Ickey Woods and his famous touchdown dance, the Ickey Shuffle. Will a player pay tribute to the dance?

It speaks so much to modern meme culture that you get a better payout for saying no than yes. That’s right: The sportsbook offering this bet believes it’s so likely a player (ahem OBJ ahem) will do the Ickey Shuffle to turn themselves into a GIF they’ll only pay me $7.86 if it happens.

Forget that. I’m looking at “NO” as a gift and betting that way. As much as I want an Ickey Shuffle, I gotta root against it.

I bet $11 on NO ICKEY SHUFFLE to win $11 (total payout $22)

5 | What will be said first during any commercial?

Bitcoin -120
Metaverse -110
NFT +500
Ethereum +1200

There are a lot of bets at the sportsbooks this year related to crypto. It sure feels like everyone sees this as the crypto Super Bowl… which so clearly hearkens back to the dot com Super Bowl of 2000 it’s absurd. That might be the biggest sign of the crypto bubble getting ready to burst yet.

I didn’t want to overload this list with crypto prop bets, so I went with this one — and I really like my odds here. I would’ve guessed “NFT” if this weren’t a multiple choice question; then I saw the odds and I get +500 on NFT. Easy call there.

I bet $11 on NFT to win $55 (total payout $66)

6 | What Anheuser-Busch brand commercial will run first?

Budweiser +170
Bud Light Next +200
Michelob Ultra +400
Cutwater Spirits +450
Bud Light Seltzer Hard Soda +600
Michelob Ultra Organic Seltzer +700

I use this bet every year to learn about the newest Anheuser-Busch products. Whatever happened to Bon and Viv hard seltzer, which they ran as their first commercial during the “hard seltzer Super Bowl” (every Super Bowl has its associated product bubble, I guess?) in 2019.

This is another one where I really like my options. My eyes went straight to Michelob Ultra, where there’s been a lot of hype around a Big Lebowski-themed ad this year. I hope A-B wants to push that to the largest possible audience. We’ve come a long way from the days of Dilly Dilly.

I bet $11 on MICHELOB ULTRA to win $44 (total payout $55)

7 | Which artist will perform first at halftime?

Mary J. Blige +150
Kendrick Lamar +225
Snoop Dogg +300
Dr. Dre +450
Eminem +500

Instead of the annual “which song will be first” question, this year we get the “which artist will be first” question. I guess with five artists doing the halftime show, the odds list on “first song” would’ve been about 50 songs long.

I’ve decided to go with Dr. Dre. Why? I’m banking on California Love as the first song (and hoping Mary J. Blige doesn’t sing the “Caaaalifornia Luuuuuuve” opening). Dre’s verse is first in that song. I say he performs it, then basically ducks out of the halftime show until the end.

I bet $11 on DR. DRE to win $49.50 (total payout $60.50)

8 | Will Snoop Dogg smoke on stage?

Yes +110
No -145

This is another bet with wild “sign of the times” odds. You only get a modest payout if an artist smokes weed during the Super Bowl.

I know we’re in California, marijuana is legal, and smoking is Snoop’s brand. But… I also know this is the Pepsi NFL Halftime Show, sanitized for your enjoyment. Everything about the show since the nipple has been choreographed down to the screws (minus an occasional rogue dancer in a shark costume). There’s just no way the NFL would be cool with Snoop smoking, and I don’t think 50-year-old Snoop is rebellious enough anymore to improvise it on show day. So I’m betting against that smoke.

I bet $11 on NO to win $7.59 (total payout $18.59)

9 | Total headline artists wearing sunglasses during the halftime show?

2 artists +150
1 artists +175
3 artists +225
4 artists +400
5 artists +600

I like this question quite a bit as my final halftime show prop. Here’s how I see it…

  • No chance at all 5. Eminem doesn’t wear sunglasses.
  • Snoop will almost certainly wear sunglasses, he basically always does.
  • I don’t think Kendrick Lamar will wear sunglasses either. He rarely does in concert and I think it’s more important for him to get his full face on camera; while he’s clearly famous, he still has room to move up.
  • I also don’t think Dr. Dre will wear sunglasses. He’s embraced his age and basically outgrown sunglasses at night.
  • And that brings us to Mary J. Blige. She’s a real toss-up when it comes to wearing sunglasses or not on stage. Looking through YouTube, it’s truly 50-50. But I’m going to lean “no” here, thinking she won’t want to hide during this moment.

I bet $11 on 1 ARTIST to win $19.25 (total payout $30.25)

10 | How many commercials will have a dog in them?

Over 6.5 -EVEN
Under 6.5 -130

Ooh this is a tough one. Really good job by whoever set this line. It’s really tempting to go “over” — in a normal year. But this is the crypto Super Bowl. Crypto commercials aren’t going to focus on dogs or other simple life pleasures. They’re going to focus on more epic themes than that — basically how going “to the moon” with crypto bets is a bigger achievement than when we went to the actual moon.

I bet $11 on UNDER 6.5 DOG COMMERCIALS to win $8.46 (total payout $19.46)

11 | Which will be higher: Biden disapproval rating or total Super Bowl points?

Biden average disapproval rating -140
Super Bowl LVI total points +100

Well kind of a bummer note to end this on, but what can you do?

This sportsbook says the disapproval rating is based on President Biden’s average on FiveThirtyEight, which currently stands at 52.6%. The over-under on Super Bowl total points is 48.5 points.

It’s going to be close. But this is a Super Bowl focused on offense, so I like the over. I don’t see the Biden score changing much; the media has that narrative locked in rock solid. So I’m taking the Super Bowl.

I bet $11 on SUPER BOWL POINTS to win $11 (total payout $22)

If (check that, when) I win all my bets, I stand to make $298.02. Maybe I’m the one going to the moon in the crypto Super Bowl.

I’ll be back next week to cover the results of these bets.