‘90s TV Shows I Wish I Could Have Bet On

Hit TV Shows in the ‘90s

There’s nothing like the marriage of entertainment and monetary gain. I suppose that’s already doable with sports betting, but I’m talking about true entertainment betting.

Some people tend to think that only involves celebrity prop bets and betting on reality TV shows like Survivor and Big Brother. While you absolutely can bet on those things, you can also bet on Game of Thrones death odds and what happens next on The Walking Dead.

I remember not too long ago there were a bunch of True Detective props, and pretty much anytime a hit series is trending, the other top novelty betting websites are right on top of it.

Not to sound spoiled, but I wish we’d been able to bet on our favorite television shows back when I was growing up. I know, technically during my formative years, I personally wouldn’t have been able to place money down on shows (this would be during the 1990s if the title didn’t give it away).

But I would have wanted the illusion of being able to cash in on my favorite shows.

What those would have been in the ‘90s can differ per person, so I’ll be forthright in admitting these are my personal favorites. Here are the 1990s TV shows I wish I could have bet on and why.

Home Improvement (1991-1999)

Tim Allen at his finest, in my opinion. The man known as Tim “The Tool Man” Taylor was the highlight of my week when I was younger. He had a fun dynamic with his wife and three sons, while he put on a fun caricature of what men were supposed to be.

Add in the weird conversations with Wilson from behind the fence and the hilarious situations Tim would get himself in, and this show had it all. There were even some emotional moments that taught some life lessons.

The Prop Bet I Wanted: Will Wilson Ever Show His Face?

There was plenty to take from almost a decade of Home Improvement, while there were rumors that the show honestly could have kept going. The biggest question mark, though, was whether we’d ever get to see the face of Tim’s neighbor, Wilson.

Wilson, the odd neighbor with sage advice, was always hidden by his fence, brush, sheers, or something else. Whether initially intended to last the series, Wilson’s hidden face stayed that way through the duration of the series.

The actor who played Wilson did show his face for a bow during a curtain call in the final aired special, but it wasn’t the same. Regardless, bettors could have wagered whether or not Wilson’s face would ever show.

Technically, the “no” side would have won, but it’d be interesting to see if the top entertainment betting sites would have honored the other side thanks to the special finale.

Family Matters (1989-1998)

Another show that often hit home surprisingly hard and also delivered the funny was Family Matters. The legendary Steve Urkel high-jacked an otherwise touching and versatile family show, but it all somehow made sense in the end.

I may be alone here, but I never felt like Urkel was the best character in this show. Instead, it was Carl Winslow, who looked over his family as a caring father but also knew when to stand his ground.

There was a humorous side to his persona, though, as he and Urkel had quite the unique relationship.

There could have easily been a prop dealing with whether or not he’d ever kill Steve, but that’s a bit too dark and was obviously never going to happen. Instead, I’ll keep things light.

The Prop Bet I Wanted: Will Steve and Laura Get Married?

This idea poked at us for the entire series, but for the longest time, Laura rejected Steve, and this was a literal impossibility. While the two never officially got married, they were engaged as the show ended, and a 10th season was rumored to feature a wedding.

Unfortunately, Family Matters got cancelled before we could hit the “yes” side of this make-believe prop bet. I’m sure bettors would have been miffed had they been able to wager on the mere possibility, but I’m just annoyed we never got to bet on the show at all.

The Fresh Prince of Bel-Air (1990-1996)

One of my favorite shows growing up was Fresh Prince, which featured a young Will Smith and an incredibly underrated supporting cast.

All these years later, Smith is the only actor from this series that found high-level success, yet Philip Banks, Carlton Banks, and Hilary Banks were hilarious characters.

Still, Will was the main focus of this series, and he played a huge hand in a perfect blend of hilarity and sobering racial topics.

The Prop Bet I Wanted: Will Will Get Married?

It’s a cliche storyline, but Will Smith’s character had a litany of love interests and was a bit of a lady’s man. Just when you thought he would settle down a bit, it was on to the next girl.

As he grew up a bit in the show, it became a more realistic possibility that with his maturity he could get hitched. Had you enjoyed that wager, you would have had a near-miss. Will does almost marry his girlfriend, Lisa, in the final episode in season five.

The X-Files (1993-2002)

Another “will they or won’t they” debate was sparked in the sci-fi thriller The X-Files, where agents Mulder and Scully worked together to figure out the paranormal. They also had an unspoken connection that grew tighter and more tense as the series wore on.

It eventually turned romantic, but for quite some time, fans of The X-Files were busier pining for it to happen than appreciating one of the best shows on TV.

The Prop Bet I Wanted: Does Mulder Find His Sister?

I could have gone with something deep involving Mulder’s “I want to believe” approach or the relationship between Mulder and Scully. Heck, who said I had to limit myself when it comes to X-Files prop bets, am I right?

I won’t spoil anything here, as the fate of Mulder’s sister is known at this point. However, a prop dealing with this previous mystery would have been great, and now that it’s out there, it could have even been profitable.

Normally, I’d just spill the beans on what happened with a show from the ‘90s. However, with a show that has since come back to TV and has also dabbled in the big screen, I’ll leave this prop open-ended. That doesn’t change that fact that we should have been able to bet on the X-Files all this time, though.

Friends (1994-2004)

It’s time for a more light-hearted turn. Friends dominated NBC for an entire decade, showing the evolution of various relationships as a group of people navigated their lives in the busy NYC scene.

Sometimes realistic and always hilarious, Friends allowed us to fall in love with an ensemble cast that truly didn’t have a weak link. It also produced one of my favorite GIFs for daily fantasy sports.

If you want to be a bit more contrarian in DFS, you pivot off of a popular option and use someone at a similar price that fewer people will use. In short, you do this.

I do all I can to try to cram that into a post once a month. My editor doesn’t seem to mind it yet.

The point here is Friends stood the test of time. It was fairly authentic, it was emotional, and it was definitely funny.

Rachel, Monica, Phoebe, Joey, Ross, and Chandler all left their own impressive mark, but together, they were an impressively cohesive group that left us wanting more even after 10 seasons.

As fun as Friends was, it could have been even more fun if we could have bet on it. There was plenty to work with here, too. Did Ross and Rachel ever get married, would Monica and Chandler get divorced, would Joey ever get married or have kids? And the list goes on and on.

But during the show, there would have been one prop that would have trumped all others.

The Prop Bet I Wanted: Will a Friends Main Character Ever Die?

Seems harsh, but with the show going on a full decade of airing, it wouldn’t have been crazy to shake things up a bit.

I know, I know, rattling a star-studded cast and going in a different direction by killing off one of the main characters would have been a reach. But that’s a turn shows take all the time these days, and at least for entertainment betting purposes, it’d have been rather captivating.

I’m sure Vegas would have priced the “no” side at -7500 and the “yes” at +9000 just to generate interest. You could even hand out separate prices for each main cast member to spice things up a bit.

Again, I didn’t want a Friends character to die, but it’s rare in television that somebody doesn’t get written out of a show or killed off. It was never likely to happen in a sitcom, but it also wouldn’t have been unprecedented.

The Simpsons (1989-Forever)

Now that I think of it, you literally could start piling up a ton of Simpsons prop bets right now, seeing as the long-running show is still going strong with no end in sight.

The show could literally go on forever, too. Given technology and the ease of replacing voices instead of actual actors, a cartoon-based television series technically could last for as long as the studios want it.

While it will probably go off the air at some point, there may actually still be room for some Simpsons betting opportunities. But I’ll look back on a wager I wish I could have taken advantage of when I was younger.

The Prop Bet I Wanted: Will Bart Kill Sideshow Bob?

If you’re feeling extra saucy, you can spin this one around and bet on whether or not Sideshow Bob would (will?) kill Bart Simpson.

It’d be a bold move to kill off their main character, but I’m sure The Simpsons could just come back the very next episode and pretend it never happened.

Cartoons and all.

Still, one of the long-running storylines is the endless battle between Bart and the psychotic Sideshow Bob, who is always plotting a new way to murder his nemesis.

There is an odd kinship between the two even though there’s evil embedded in their connection, so it isn’t crazy to think The Simpsons could eventually force one or the other to finally fully triumph.

While it might be silly to eradicate such a fun character for good, it sure would have been (and would be) fun to bet on whether or not it could happen.

Seinfeld (1989-1998)

Lastly, I come to my favorite show of all time and arguably the best TV show of the 1990s, Seinfeld. Jerry Seinfeld led a brilliant cast of characters with an ever-growing line of side characters that were honestly just as iconic when it was all said and done.

There wasn’t a ton of substance on a real level with Seinfeld, but its comedy stands the test of time, and the relationship and societal questions raised still ring true.

Seinfeld was groundbreaking and relatable, while also downright silly. It also could have given way to more entertainment prop bets than possibly any show during the ‘90s.

Of all the potential Seinfeld prop bets, though, one arguably stood tall above the rest.

The Prop Bet I Wanted: Will Jerry and Elaine Get Back Together?

Maybe one day this is finally answered for us in the form of a true Seinfeld reunion. Jerry Seinfeld did say that it is possible, after all. But until that happens, I’ll always wonder what could have been with the dynamic between Jerry and Elaine and if they belonged together.

Okay, it’s not consuming me or anything, but it certainly would have been fun to bet on it.

The beauty here is with all of the main cast still alive, a Seinfeld reunion could still happen, and this prop bet and so many others could actually become reality. In fact, perhaps at some point, your favorite novelty betting sites will offer a Seinfeld prop about whether or not the show returns.

Now that is something I’d like to bet on.


It’s fun to look back at some old TV shows from the 1990s and ponder some fun props that could have existed. You could probably add to the pile with a long line of iconic television series, and I’m sure you wouldn’t have to restrict it to just one decade, either.

The ‘90s were a golden age for the sitcom, but television has evolved since then. Netflix and Hulu now stretch the boundaries, and while there is a surprising lack of television show prop bets, more and more will pop up as time goes by.

I still wish we all could have cashed in off some of those legendary shows, but here’s to doing just that with some of the best shows moving forward.


‘90s TV Shows I Wish I Could Have Bet On

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‘90s TV Shows I Wish I Could Have Bet On


With the rise of entertainment betting opportunities on hit TV shows these days, here’s a look at shows from the 1990s that would have been fun to bet on.


Noah Davis

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