The unique and extremely popular [citation needed] authority on pop culture since 2008

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written by Sam Greenspan

For the 15th year in a row, I bet real money on ridiculous Super Bowl bets about Tom Cruise, Drake, Rihanna, commercials and more.

It’s my 15th year of making ridiculous Super Bowl prop bets. And making real money bets on them. I was doing this long before it was cool. (Or increasingly legal.)

So even though I haven’t written anything else on this site since last year’s Super Bowl (although some updates ARE in the works!), I can’t skip out on this tradition.

However, this year I will not be able to watch the Super Bowl live. To really twist the knife on the passage of time from when I started this website until now, I’ll be on a family vacation this Sunday and won’t watch the game (or commercials) until I get back.

Last year I went 4-7-0 on my bets, losing $46.28. That took my lifetime record to 71-75-8 and -$209.96. But I put in more than half of that money in 2008. Adjusted for inflation, that’s at least $285. The 2008 version of me would’ve loved to spend all that on Bud Light Lime and Facebook gifts.

1 | How long will it take Chris Stapleton to sing the U.S. national anthem?

Over 125 seconds: -120
Under 125 seconds: -120

The sportsbooks I use are all over the place on this, likely because Stapleton doesn’t have a long history of anthem performances from which to draw.

The books all around the two minutes and change mark, but the odds are inconsistent. Locking in at -120 was my best odds on the over. Because it’s my policy to bet the over. I’ve sustained this bit for 15 years thanks to betting the over. Last year I didn’t and it burned me. Nothing was keeping me from the over this year.

I bet $11 on over 125 seconds to win $8.80 (total payout $19.80).

2 | Will Tom Cruise parachute into the stadium and hand deliver the game ball to the referees?

Yes +2500
No -15000

I mean… what? Might as well call me seven cents richer.

I bet $11 on no, Tom Cruise won’t parachute into the stadium like the Fan Man, to win $0.07 (total payout $11.07).

3 | Drake curse: What team apparel will Drake be wearing on Super Bowl Sunday?

Kansas City Chiefs -350
Philadelphia Eagles +245

Drake is famous for riding bandwagons and causing them to crash. So who will he curse for this year’s Super Bowl?

I looked him up for the first time since someone said, “Hey you know that new rapper Drake? He was on Degrassi” and turns out he bet big money on the Chiefs in the AFC Championship a few weeks ago. Since he won, I assume he’ll stay consistent and bet the Chiefs again. The odds are bad (-350 for Chiefs versus +245 for Eagles), but the outcome is steady.

I bet $11 on Drake wearing Kansas City Chiefs merch on Super Bowl Sunday to win $3.14 (total payout $14.14).

4 | First TV advertisement

Avocados from Mexico -450
Hellman’s +300

Two random Super Bowl advertisers in a random betting battle. That’s what Super Bowl prop bets are all about.

I see Hellman’s enlisted Jon Hamm, Brie Larson, and Pete Davidson for their commercial. Avocados from Mexico got Anna Faris posing nude as Eve in the Garden of Eden.

I feel like Hellman’s is going to push for an earlier spot, and the Puritans are going to bump the avocado ad later. Plus the Hellman’s odds are better. I’m going mayo.

I bet $11 on Hellman’s to air before Avocados to win $33 (total payout $44).

5 | What song will Rihanna perform first at halftime?

Diamonds +200
This Is What I Came For +400
Where Have You Been +450
Don’t Stop the Music +500
Stay +700
Rude Boy +1000
Umbrella +1000
We Found Love +1200
What’s My Name +1200
Only Girl (In the World) +1800
Work (+2500)
Hate That I Love You (+3000)

I see three options here.

One, Don’t Stop the Music. Feels thematically like it could start off the show. After all, it was good enough to start the Treblemakers’ set in Pitch Perfect.

Two, What’s My Name. Not only is it a “please allow me to introduce myself” song to logically kick off a big mainstream set like the Super Bowl, it’s a crowd pleaser.

And three, the high-odds long shot of Work. Could be the pick because she’s going to “work” at the halftime show. And the whole “work work work work work work work work work work work work work” intro feels Super Bowl Halftime-y.

Still, going with my first instinct. Fingers crossed for an Adam Devine cameo instead of an Adam Levine cameo.

I bet $11 on Don’t Stop the Music to win $55 (total payout $66).

6 | Rihanna exposes but cheek on stage at any point of performance

Yes -165
No +125

It appears our bookie friends haven’t gotten the memo that these bets are not cool in this day and age. Also… I’m getting a better payout on “no”? Virtue signaling AND plus odds? Sign me right the hell up.

I bet $11 on no butt cheek to win $13.75 (total payout of $24.75).

7 | How many TickTok [sic] videos will jacksonmahomes post during the Super Bowl?

Over 1.5 +145
Under 1.5 -190

I love that they spelled it “TickTok.” Place your bets, fellow kids!

Jackson Mahomes may love drafting off his brother for viral attention but he wasn’t posting multiple TikToks during the previous playoff rounds. So it seems unlikely he’s going to up his frequency during this bigger game. He also seems to do more “montage” style TikToks where he captures multiple moments in one video.

I bet $11 on under 1.5 videos to win $5.79 (total payout $16.79).

8 | What will happen to the price of Bitcoin during the Super Bowl?

Price goes up -130
Price goes down EVEN

Hey bookmakers, didn’t you hear? Last year was the crypto Super Bowl. This year the bet should’ve been “How many times will ChatGPT say its servers are too busy during the Super Bowl?”

Anyway, without any particular dog in the fight I’ll take the better payout.

I bet $11 on the price going down to win $11 (total payout $22).

9 | How many beers will be sold at State Farm Stadium?

120,000 or under -175
Over 120,000 +130

In 2019, at Mercedes-Benz Stadium, fans bought 117,400 beers. Attendance was 70,081.

State Farm Stadium in Arizona is predicting 72,200 fans. If we stick with the ratio of 1.675 beers per attendee, that takes us to 120,949.75.

And sure, the beers at the stadium this year will probably cost like $45 each, but what are fans going to do — not drink?

I bet $11 on over 120,000 beers to win $14.30 (total payout $25.30).

10 | If the Chiefs win, will Andy Reid be doused in BBQ sauce after the game?

Yes +1600
No -15000

This is another bet with terrible odds. And while we all like the visual of Andy Reid taking a barbecue sauce shower… I’m going to collect my seven cents and move on.

I bet $11 on Andy Reid not getting doused in BBQ sauce to win $0.07 (total payout $11.07).

11 | Will any player propose to his girlfriend on the field after the game?

Yes +375
No -600

I’m betting on a long shot in the name of love. And also because some player is going to want to grab that spotlight.

I bet $11 on yes, someone will propose to win $41.25 (total payout $52.25).

So there you have it. I could win $186.17 (total payout of $307.17) if and when I hit on all 11 bets. Again, I can’t watch live or tweet live this year, so I’ll be back late in the week with my results.