The Sick World of “Who Will Die First” Bets

Grim Reaper by the Hollywood Sign

I hadn’t planned on writing this article. No, I didn’t even know that you could bet on the mortality of celebrities and public figures – at least, not with a legitimate sportsbook! Well, it turns out you absolutely can, and thanks to the hilariously twisted souls behind setting the odds for, it’s more fun and less depressing than you might think.

For years I’d heard people discussing their death pools on radio shows and around the office. Usually, they were brought up as a way to publicly predict that a celebrity would be dying soon (within the year, in most cases), with little follow-through beyond the announcement.

More recently, I’d even heard of a more official death pool being organized and run by comedian Doug Stanhope – with a professional, organized website and everything! But even those options pale in comparison to what’s going on at — and I’m assuming other betting sites as well – at the moment.

Yes, “Death Matchups” Actually Exist!

First of all, the oddsmakers at are hilariously sick, which I will make abundantly clear in later sections. Not only are they setting odds on when an extensive range of celebrities and public figures will die, but they also pair them up into “death matchups,” where the follow-through picks which of two or more options will croak first.

It’s how the bookies decide to make these pairs that really shines a light on their inappropriate brilliance. For example, setting up a head-to-head between Demi Lovato and Artie Lange is breathtakingly insensitive. These two have nothing in common outside of heroin addictions and recent hospitalizations.

To reword the wager, it’s essentially “which of these two troubled celebrities will die of an overdose first?” Pretty dark, huh?

Of course, they never come out and say, “This is our heroin showdown,” that would probably be frowned upon. They just set the lines and leave the rest for you to figure out. And while, the whole thing is perhaps pretty mean, especially in today’s hyper-sensitive world; why shouldn’t we put our money where our collective mouth is?

It’s not like we aren’t all hypothesizing this sort of thing with our friends and colleagues all the time. This just raises the stakes a bit. Makes your “I told you so” a smidgen more rewarding.

The Predecessor: Death Pools

As I mentioned in the intro, death pools have existed in the zeitgeist for years. Think of them as a mix of fantasy sports and pop culture, with a sprinkle of the macabre for good measure. Participants choose between ten and twenty public figures whom they believe will pass away during the year, and receive points for every correct prediction.

When a celebrity dies, you subtract their age from 100, giving you the total point value. That way, you’re incentivized to take some risks on some younger picks rather than filling your roster with the elderly. Whoever scores the most points at the end of the year, wins.

The problem with death pools is that there aren’t many professional organizers. These have usually been left to small office pools or groups of friends who track and score all of the deaths themselves. What has done is to bring death pools to the mainstream, and with a more sports-betting-esque twist.

1-on-1 Death Matchups

The oddsmakers at offer celebrity death betting in a couple of different formats. In some cases, they’ll set lines on a small field of competitors with a unique variable in common. Other odds are available on a single celeb and whether they’ll outlive a specific date or situation (such as a prison sentence).

In this section, we’ll be looking at the online sportsbook’s head-to-head death matchups – which make up the majority of their morbid wagering opportunities. All the bettor must do is pick whichever star they believe will die first. Let’s take a look at what they’ve got on the board!


As a quick aside, before I actually breakdown and handicap these matchups, I feel like I should offer a trigger warning of some kind. There’s just no way to speculate on people’s upcoming deaths without being somewhat offensive. Some of these celebrities have had drug problems, mental health issues, and a whole range of factors that could potentially play a role in their demise. I have to consider those when making my picks in the same way I look at a quarterback’s completion percentage for NFL betting.

Betty White (-260) vs. Carol Burnett (+200)

We begin the festivities with a contest between two geriatric comedy icons: Carol Burnett and Betty White. At 97-years-old, White is twelve years her opponent’s senior, which explains why the Golden Girls star is such a heavy favorite at –260 odds.

According to the “Life Expectancy” stats from the CDC, only 7% of white women live to be Carol Burnett’s age. That number drops to 3.3% of the population that sees as many birthdays as Betty White has.

However, both of these women have already well-exceeded the average life expectancy in the US (78.6), tells me that this may not be as one-sided as the lines suggest. They’re both in rarified air as it is, and quite frankly, after 80 I’m pretty sure you’re basically just taking it “one game (day) at a time,” like every athlete always says.

The being said, Burnett looked fantastic and sounded sharp as could be at the 2019 Golden Globes in January, where she received an inaugural lifetime television achievement award that’s was named in her honor. I mean, there were no signs of slowing down.

But Betty White seems to be going strong still as well. She was back to work lending her voice to 2019’s Toy Story 4 after staring in a documentary about her life and career just last year. Back in 2017, White also acted in two episodes of “Young & Hungry,” and played herself in the TV film “If You’re Not in the Obit, Eat Breakfast.” That’s still pretty active.

Because both actresses have surpassed the average life expectancy and are relatively similar in other measurables, I’m making my pick based on value exclusively. At –260 odds, I’d have to believe there’s higher than a 72.22% chance of Betty White passing first. I’m leaning closer to it being 60/40, which makes:


Carroll Burnett at +200 the bet to make.

Charlie Sheen (-200) vs. Magic Johnson (+160)

See….this one is nuts. To be perfectly honest, I don’t think I even want to highlight what these two men have in common other than living in Los Angeles. There’s just no fun way to do it, and I’m sure you can figure it out. I’ll give you a hint, “tiger blood,” as Charlie loved saying during his little war with Hollywood back in 2011.

This matchup seems relatively obvious to me. While Magic Johnson’s diagnosis came a couple decades before Sheen’s, we’ve seen nothing during that time to suggest the NBA superstar’s health is suffering in the least from his disease. Plus, Magic is much more stable psychologically and was a professional athlete most of his life rather than a drug-addled actor.

But more than anything else, I believe this wager will come down to one thing – and one thing only: crack cocaine. Only Charlie Sheen has gone on mainstream television and bragged about his incredible constitution for taking massive amounts of coke in its smokable form.

Now, Johnson is both six years older than Charlie and significantly taller. It’s a well-known fact that larger people die at a younger age. But somehow, I feel like height is less of a contributor to early deaths than a history of alcoholism, hard partying, and frequent crack smoking.

Both of these men have the resources to keep their viral loads below any detectable threshold, so the variable that brings them together is unlikely to be the determining factor in settling this death match.


For that reason, I have to pick Charlie Sheen to die first at –200.

Regis Philbin (-105) vs. Bob Barker (-135)

One thing that has been made abundantly clear to me working on this article is that rich people live to be very old; although I suppose I was already aware of that fact. Whatever the case, this matchup is a depressing one – pitting two beloved public figures/game show hosts against each other.

Regis, the Guinness World Record holder for “most time spent on a television camera,” is best known for his time on Live! With Regis and Kathie Lee/Kelly and Who Wants to Be a Millionaire. He is currently 87-years-old and has experienced the following health issues:

  • 1993 – angioplasty
  • 2007 – triple bypass surgery to clear plaque in the arteries
  • 2009 – hip-replacement surgery
  • 2010 – had a blood clot removed from his calf

Bob Barker is a key figure in American culture; most notably for his time spent hosting The Price is Right, which he did from 1972 until his retirement in 2007. Barker is further celebrated for his cameo in Adam Sandler’s Happy Gilmore, in which he got into a fist-fight with the lead character in the film.

Mr. Barker is a slight favorite in this matchup, despite being 95-years-old, a full eight years older than Philbin. Here are the famous host’s health scares throughout the years:

  • 1982 – herniated disk and sciatica
  • 1991 – mild stroke
  • 1999 – partially blocked left carotid artery
  • 2002 – stroke and prostate surgery
  • 2015 – tripped and fell
  • 2017 – tripped and fell
  • 2019 – tripped and fell

Based on the medical histories, I’m reluctantly laying the $135 to win $100 on Bob Barker.

With multiple strokes and a recent history of falls — resulting in either trips to the emergency room or paramedics being called – the price tells me to take the older of the two living legends.

Rosie O’Donnell (-150) vs. Rosanne Barr (+110)

I’m guessing the motivation behind pairing Rosie and Rosanne together is that they’re both somewhat heavy-set, brunette, middle-aged comediennes and television personalities with “Ros-” in the front of their names. They’re also each known for being brash and opinionated, having both seen their fair share of controversies throughout their respective careers.

While O’Donnell is the younger of the two at 56, I tend to agree with the oddsmakers on this one – that she should be the betting favorite. The former The View co-host suffered a heart attack with a 99-percent arterial blockage in 2012. Plus, she seems more high-strung than Barr, in general.

While Rosanne’s life has definitely gotten more stressful recently – mostly due to various tweets and comments, she said while allegedly on Ambien. She was thrown off her hit show’s reboot and seemingly banished from stardom as a whole after her online ramblings took a racist tone. Still, I’m riding with the 66-year-old Rosanne Barr to outlast her counterpart in this matchup.

She had gastric bypass surgery in the late-1990’s and has done an excellent job keeping the weight off. Roseanne also owns a macadamia nut farm in Hawaii, which is serene — I’m sure — and helpful in dealing with stress.

The Ambien usage is not ideal.


However, I’m still picking Rosie to croak first at –150 gambling odds.

I’m betting on Roseanne’s more laidback demeanor, despite neither side of this wager feeling like a sure-thing.

Demi Lovato (-130) vs. Artie Lange (-110).

I mentioned this matchup in the introduction because it’s just so messed up. The only thing in the world these two entertainers have in common is heroin. That the 26-year-old Lovato is the favorite versus Artie – who may be the biggest mess of a human being I’ve ever observed in my life – despite being twenty-five years younger is especially sad.

However, while Lange is much older, Demi’s age raises red flags for reasons other than the aging process. The actress and pop-singer will be turning 27 in August of 2019, the age at which so many other celebrities have been lost tragically.

With a history of self-harm, bipolar and eating disorders, and now heroin addiction, she’s currently in that make-or-break moment in her life where she’ll either pull out of this and get her life on track or likely flame out.

It doesn’t help that she’s up against a man that probably should have died fifteen years ago, based on his lifestyle and approach to life. As the second mic on the Howard Stern Show, Artie was arguably one of the hottest comedians in the country in the early-to-mid 2000s, and one of the most hilarious radio personalities of all-time.

Unfortunately, the comedian also has a dark side dating back to an accident that left his father a quadriplegic in Lange’s late teens. Before being hired by Stern, Artie had already let cocaine and booze cost him a role on MadTV and had been to rehab.

He kept it together for a couple years on the radio before the early morning work hours mixed with weekend stand-up comedy dates all over the country on weekends took their toll. His weight ballooned uncontrollably while Lange became less reliable on the Stern Show. Eventually, Artie admitted that he’d developed a heroin addiction in a tearful apology on air.

Since then, the former star has been in a never-ending cycle of addiction, arrest, and apologies. Current pictures show that his nose has completely collapsed from all of the drugs. Based on his current appearance and obvious ongoing usage, I’ve been anticipating poor Artie’s death on an almost daily basis for at least six months now.

But that’s the thing, he always keeps on truckin’ somehow, against all the odds. Is it possible that Demi Lovato’s troubles could get to her first? I just can’t bring myself to say “yes” to that. I’m going to root for the young lady; Arthur has been given more than enough chances. At this point, I don’t see any way Artie makes it to August when Demi will be turning 27.


Give me Lange at –110.

Jay Leno (+120) vs. David Letterman (-160)

The battle of the late-night juggernauts who competed for Johnny Carson’s Tonight Show, before going head-to-head in the ratings for the next few decades. Letterman was the heir apparent at NBC and host of Late Night when Carson finally retired in 1992. The legendary Tonight Show host openly wanted to pass the show to Dave, but network execs went with Leno instead.

Letterman had given Jay a platform by frequently bringing the stand-up comedian onto Late Night, which is why the eventual decision was taken as such a betrayal. Their rival persisted from that point forward, with Letterman moving to CBS and taking the occasional shot at his former-guest-turned-enemy throughout the years.

While Dave’s CBS show was always the more critically acclaimed, Jay Leno dominated the ratings war for the vast majority of their rivalry. Unfortunately, I predict the losses to Jay will keep on piling up for Letterman, even in retirement. At 71, Letterman is three years older and already required quadruple bypass surgery in 2000.

Furthermore, Dave always seems somewhat miserable, as if he’s carrying the weight of the world on his shoulders. In contrast, it’s not clear if Jay Leno experiences human emotion at all. He seems to just play with his cars, do tons of stand-up, and let everything roll off his back. I’m not sure there are enough layers to him for depression, anxiety, or self-loathing ever even to come up.


The heart surgery, history of defeats, and demeanor are why I’m taking Letterman to go first at –160 odds.

The Single Celeb Special

When it comes to celebrity death wagers, it doesn’t always “take two to tango.” The bookmakers will also set lines on individual public figures that may be close to the end, or in a dire situation. From what I can gather, they pick their spots wisely with these bets, setting odds on personalities that have already earned the public’s ire. Having too much empathy or compassion for someone makes wagering on their end a lot less fun, after all.

Will Bill Cosby Die in Prison?

So, who better to represent this exact scenario than Bill Cosby himself (pun intended)? The betting lines for this wager are expressed in precisely the way I’m about to type them; I have taken zero artistic license:

  • Hey, Hey, Hey! -450
  • No +250

As you can see, society is taking Cosby’s death without a whole lot of sympathy. I get it, he did some absolutely monstrous things. There’s just something about gloating about people’s impending doom that’s always made me feel a little guilty. But then, what is this article if not that exact thing?

Just keep reminding yourself what he did to rationalize this perverse entertainment…

Dr. Huxtable was sentenced to 3 to 10 years in state prison and moved to his current facility on September 25. 2018. On January 28, 2019, he was transferred from “administrative segregation,” or solitary confinement, into the general population. His earliest possible release date is September 25, 2021.

At the time of writing, he’s 81-years-old. Can he survive another two-and-a-half years in “gen pop” as a convicted sex offender? Seems doubtful.


I’d have to put my money on “Hey, Hey, Hey” at –450.

Group Death Matchups

Another unique betting opportunity that is providing is the group style of death matchups. The basics are the same as before, only you’re choosing from an entire field of competitors. The oddsmakers once again group these celebrities based on common traits or experiences, then let the public pick who they think will die first.

MyBookie’s “Alleged Sexual Deviants” Death Pool

  • Jerry Lee Lews +150
  • Woody Allen +250
  • Bill Cosby +100
  • Roman Polanski +250
  • Jerry Sandusky +600
  • Harvey Weinstein +800
  • Subway Jared +1000

Yeah, what am I even going to say about this one? Blame the bookies, not me; these guys are seriously out there! I appreciate them taking the chance at being this edgy in the current social climate, but I wouldn’t have the guts to set these lines.

Either way, this bet is all about the (alleged) creeps. Some of these men have been convicted, while others have not. One court case is starting soon and yet to be determined.

If you’re reasonably confident in Bill Cosby dying in prison, this is a much better place to wager on him, where you can get +100 odds rather than –450. To me, those are excellent odds that possess positive betting value.

Another top choice would be Jerry Sandusky. Not only is he up there in age, but his crimes make him a prime target for vigilantes behind prison walls. Nobody would have a problem with the guy that murdered Sandusky; he might be treated like a hero! Dirty business.

Similarly, Jared from Subway is a decent long-shot pick at +1000 odds. He runs the same risks in lockup and would be another favorite target. His youth complicates things somewhat, but you’re usually pretty safe gambling on violence when it comes to the US prison system.


I’d put my most substantial stake on Bill Cosby, while also taking low-cost fliers on Jerry Sandusky and Subway Jared.

MyBookie’s “Football Players Tied to Murders” Death Pool

  • Rae Carruth +300
  • Ray Lewis +2000
  • OJ Simpson -1000

The last market I’ll cover in this article is all about professional football players that were involved in murder investigations. I’m guessing you’re familiar with OJ Simpson and his story. At –1000, he’s an enormous favorite to die first.

Sounds about right; while OJ is 71-years-old, his opponents are 45 and 43 years old respectively. Ray Lewis is still in prime health and is flourishing as a football commentator on Showtime. His death would be a massive shock and is highly unlikely.

Rae Carruth is a bit more interesting. After being found guilty of conspiracy to commit first-degree murder in 2001, the NFL wide receiver was sentenced to and served 18-years and 11 months in prison. That’s almost two decades of horrific nutrition, extremely high stress, and institutionalization.


At +300, Carruth is probably the only bet worth taking here.

In Conclusion

Well, that’s the wild world of celebrity death betting!

Is it extremely messed up? Absolutely. But everybody dies eventually, and if we’re really being honest, it’s not all that different from gambling on boxing or other fight sports; just a little more direct. Plus, a lot of the odds are kind of fun; only a few are legitimately depressing.

The point of this article is introducing readers to another of the many forms of sports betting available to players online. While the brick-and-mortar oddsmakers are somewhat limited, web-based operators are free to be as creative as they desire. These wacky wagers are the perfect way to keep things new and fresh when there aren’t any sporting events catching your eye.

Most importantly, saying “I told you so” is one of life’s great petty pleasures. When it comes to pop culture, death matchups — and all “Entertainment” betting lines — are the ideal way to put your money where your mouth is.

Petko Stoyanov
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About Petko Stoyanov
My name is Petko Stoyanov, and I've been a gambling writer for more than ten years. I guess that was the natural path for me since I've loved soccer and card games for as long as I can remember! I have a long and fairly successful history with English Premier League betting and online poker, but I follow many other sports. I watch all big European soccer leagues, basketball, football, and tennis regularly, and I keep an eye on snooker, volleyball, and major UFC events.