2020 Celebrity Deadpool Betting

We are living in a world where there are very few sports options to bet on. There is no NBA, NFL, MLB, or NHL, as nearly all North American sports were halted due to the Corona Virus pandemic. That has left us with a serious lack of betting action!

But what if I told you there are a plethora of other things out there that you can bet on to keep you in action while sports are away? If you head over to online sportsbook, MyBookie, they will take bets on nearly anything!

Want to bet on your favorite TV shows like Amazing Race, Survivor, or America’s Got Talent? MyBookie will take that action. How about betting on award’s shows like the Grammys and the Oscars? They offer those too. But my favorite thing to bet on right now over at MyBookie, just might be the most twisted of all, as you can bet on which celebrity is going to die first!

While betting on death might sound a bit macabre at first, death is a part of life, and if one of your favorite celebrities is going to kick the bucket, you might as well make some money from it, am I right? In this article, we are going to handicap the current deadpool betting odds currently being offered at MyBookie. Let’s get started!

Charlie Sheen vs Magic Johnson

Our first celebrity pairing features two HIV positive superstars, actor, Charlie Sheen, and basketball legend, Magic Johnson. You are going to see a trend here of celebrities being paired together for one reason or another, and this pairing is clearly because of their shared medical ailment. Oh, and one last thing before we jump into the pairings, these bets are only valid until the end of 2020. Once the new year starts, all action is considered void and bets are refunded.

Betting Odds

  • Charlie Sheen -200
  • Magic Johnson +160

Charlie Sheen -200

Not shockingly, Charlie Sheen opens as the betting favorite here. And to be completely honest, it is a bit of a miracle that Sheen survived his tiger blood antics from nearly a decade ago. For those of you that may not remember, Sheen was a longtime film star and took his talents to the small screen, where he was the highest-paid actor on television, for the nation’s top-rated show, Two and a Half Men.

Sheen screamed that even though he was making astronomical money, more than any other TV actor in history had made, in fact, that he was being underpaid. This caused a rift with his bosses, which eventually led to his being fired from the show in 2011.

After being fired, Sheen went on a media rampage, declaring that he had tiger blood, dating multiple porn stars, and gloating about how big of crack rocks he could smoke. Shortly thereafter, it was revealed that Sheen was diagnosed with HIV, and that was what was behind his epic tailspin.

Since then, things seem to have calmed down for Sheen. He has done some speaking engagements, limited acting, and charity work, but mostly he has stayed out of the public eye. Late last year, he announced that he had been sober for over two years.

Living with HIV is always a perilous situation, but Sheen still has plenty of money and seems to be in control of the disease at this point. He had embraced some controversial HIV treatments early-on, which isn’t all that surprising for the noted anti-vaxer and 9/11 conspiracy theorist, but seems to be on a more traditional route now.

Magic Johnson +160

Magic Johnson was once the face of the HIV/AIDS epidemic. When Magic came out as HIV positive in 1991, he was by far the biggest name ever infected with the virus and was the biggest basketball star in the world. At the time of Johnson’s announcement, AIDS seemed like a death sentence, and many thought he had just months to live.

But Magic has proven that wrong, as he has gone on to live what seemingly appears to be a normal life. He is a very successful businessman, making far more money off the court than he ever did on it, and is a regular TV show personality, covering the NBA among other sports, and is a partial owner of the Los Angeles Dodgers Major League Baseball team.

Johnson continues to be a major face of HIV and has helped dispel a lot of rumors and misinformation about the disease. He founded several charitable organizations, and is at the forefront of HIV medical research, championing several different anti-viral drugs.

The Bet

This is an interesting bet. Had you asked this question in 1992 right after Johnson announced he was HIV positive and Sheen was dazzling on the screens in films like Young Guns, Johnson would have been an enormous favorite to go first.

On the flip side, had you asked this question in 2012, after seeing Sheen meltdown in a flurry of cocaine, hookers, and booze, he would have then been the big favorite.

But now that both guys have seemingly gotten through the worst of their initial diagnosis and reactions, this seems like a fairly even matchup. Sheen is deservingly the favorite, as his sobriety is a bit tough to believe, and he has lived a far more reckless life in general, before and after his HIV diagnosis, than Johnson, who spent much of his life as an elite athlete.

At even money, I am likely backing Sheen. But at this price, I think backing Magic is the value side. I know that Magic is in much better physical shape, but he is also a full six years older. Both guys have their HIV well under control, so that cancels each other out. At this point, I am backing Magic because of his advanced age, which should be a major factor in any deadpool bet.

And while it is unlikely that either guy will actually die this year, with the COVID-19 outbreak attacking immune-compromised people the hardest, this could absolutely be a bet that ends up paying out. 2020 has been all about maximum pain so far, and if Magic were to pass, it would be yet another national tragedy. But hey, if it is going to happen, it is going to happen, might as well get paid. Give me Magic in the deadpool bet is a big upset over Charlie Sheen!

The Bet
Magic Johnson

Bob Barker vs. Regis Philbin

Our second matchup features two guys know for their long runs as game show hosts and TV personalities. Both of these guys are well up there in age, with Barker coming in at 96 years old and Regis clocking in at a venerable 88 and have been out of the public eye, and enjoying retirement, for quite some time.

Betting Odds

  • Regis Philbin +125
  • Bob Barker -165

Bob Barker -165

Bob Barker was a staple of television for over fifty years. Some of my favorite memories growing up were staying home “sick” from school and watching The Price is Right with my mom. Barker was on some form of TV from 1956 all the way through to his retirement in 2007. He has also made several TV and movie cameos, mostly appearing as himself over the years, including a hilarious role in the Adam Sandler classic, Happy Gilmore.

But the end is growing near for Barker as he is now 96 years old and has been battling health issues in recent years. He was in and out of the hospital several times last year for back issues that have kept him in a wheelchair. And he has had a long battle with skin cancer that has been treated effectively over the course of the last decade. At this point in his life, even in relatively good health for his age, it is hard to imagine Barker being around too much longer.

Regis Philbin +125

Another great memory from my youth was listening to Regis Philbin proclaim, who wants to be a millionaire, on his hit primetime game show. Regis had a great way of creating drama on the show, and when he would ask the competitors if that was their final answer, he had the unique ability to get people to change their minds immediately. It was must-see TV and captivated the nation.

Similar to Barker, Regis has had a great run, and at 88 years old is nearing the end of his run as one of America’s most beloved personalities. Philbin has had a well-documented struggle with heart disease, and at his age, that is not a diagnosis that you want to hear. Heart disease is the biggest killer in the US, and Philbin had his first angioplasty in the ’90s and had triple bypass surgery in 2007, and he continues to battle the disease to this day.

The Bet

I don’t take a lot of celebrity deaths to heart. To me, celebrities are just people, and I tend to react to their deaths no differently than any other person. That being said, when these two guys go, it’s going to hurt. So much of my childhood surrounded seeing these guys on TV every day, it’s almost like they helped raise me just a little bit.

And while it hurts me to take a stand on this one, I am backing the favorite, Bob Barker. While a play on Philbin, an 88-year-old man with heart disease, getting dog money, seems to be a juicy proposition, I just can’t hide from the fact that Barker is ninety-six years old.

People just don’t live past 96-years old very often, and that age gap must be the main driver in this bet. The truth is that both of these guys might not see the other side of the Corona Virus pandemic, as it is feasting on our older generation. But if I am making a play, I am laying a little wood and making it on Barker.

The Bet
Bob Barker

Rosie O’Donnell vs Roseanne Barr

The battle of the Rosie’s is up next as we take a look at the odds between talk show host and TV personality Rosie O’Donnell and actress Rosanne Barr. O’Donnell is surprisingly the betting favorite, despite being nearly a decade younger than her counterpart.

Betting Odds

  • Rosie O’Donnell -150
  • Roseanne Barr +110

Rosie O’Donnell

Rosie O’Donnell is no stranger to controversy. She is a fiercely liberal and outspoken advocate for gay rights and has spoken out against President Donald Trump and previous President George Bush on many occasions. Rosie rose to fame, pun intended, with her daily syndicated talk show The Rosie O’Donnell Show and then spent time on daytime talk show, The View.

Rosie has been working consistently ever since, with various gigs including a Sirius XM Radio show, and Showtime comedy series SMILF. But health has been an issue for Rosie as she has battled with obesity and even had a heart attack in 2012 when she was just 50-years old. O’Donnell is now 58-years old and has lost much of her weight, as she is currently a relatively healthy 185-pounds.

Roseanne Barr

I guess there is just something about that Rosie name that draws controversy, as Roseanne has been embroiled in some form of controversy or another for the last forty years in the public spotlight. Roseanne became a household name when she stared on her self-titled sitcom in the late-eighties and nineties.

She returned to TV in 2018, to huge acclaim, only to be fired shortly thereafter, after sending out what some people called a racist tweet. Similar to O’Donnell, Barr has also had more than her fair share of health struggles as she is diagnosed autistic, has weighted as many as 350-pounds, and reportedly had a heart attack in 2018, although she later denied that it ever happened.

The Bet

I am shocked to see O’Donnell as the favorite here. Roseanne is nine years older and reportedly had a recent heart attack. She has a history of severe mental illness and had a very public meltdown in 2018 after her firing from her show. Both women are overweight and have struggled with obesity in their lives, and both have a history of heart attacks, so in my estimation, the fact that Barr is nearly a decade older makes her the clear play here. I’ll back Barr and pick up some juicy dog money along the way!

The Bet
Roseanne Barr

Wrap Up

No sports to bet on? No problem! Just cruise over to MyBookie and check out their celebrity and entertainment betting section where they have all kinds of stuff you can bet on. Thanks for reading and make sure that you stay tuned to The Sports Geek for all of your sharp betting advice!

Jason Gray / Author

Jason is a true Las Vegas insider as he has called the sports betting capital of the world his home for sixteen years. Jason started out his career in gaming by running the biggest poker tournaments in the world and managing some of the biggest sportsbooks on the strip. Jason has transitioned out of casino operations and has been covering sports betting for the sports geek for just over two years. His main focus is on baseball, college basketball, and the NFL