The 5 Most Enjoyable Kinds of Sports Bets You Can Make

5 Most Enjoyable Sports Bets

Reading this could be dangerous to your health.

We’ve established that sportsbooks rely on bettors picking teams and outcomes for pleasure, not because the bettor has methodically thought through the potential results.

While boring “system” bets on 5-innings outcomes in baseball or O/U outcomes in American football can be the secret to keeping a profitable betting account, those bets aren’t always a lot of fun.

I believe that skipping out on every opportunity for fun (and cheering in-person or at a TV) turns sports gambling into a pointless, losing exercise. But a literally losing exercise – one where the bettor loses all kinds of money and has to give it up or upload another healthy cash deposit – is also a bummer.

My advice is to open a pair of accounts at different books, with the goal of increasing the “boring” stake steadily with systems bets while splurging on long-shot wagers with the other.

But there’s a difference between splurging and simply “urging” the bookie to take your money. Even while making small gambles, it’s possible to burn through a big deposit in no time if you’re just picking out markets that seem the most entertaining.

Thankfully a big part of the fun is handicapping potential wagers.

Don’t get the wrong idea – I’m not actually handicapping any long-term “value” strategies for betting today. None of the most pleasurable sports gambles pay off as well as those 5-innings system bets. Handle with care!

Learn how to make intelligent high-risk bets without simply throwing your stake away. Here’s a primer on some of the most enjoyable betting markets out there…and how to interact with them without giving the bookmaker a gimme.

Most Enjoyable Bet #1: The Gridiron Parlay

I’ve spent many years trying to figure out why American pigskin is such a wildly-popular gambling sport. I think it has something to do with the rhythm of the game.

From time to time, there’s a push to “make football games quicker” at the college or NFL level. It strikes me as the same kind of lunacy that causes golfers to obsess over playing a round in 3 and ½ hours instead of 4 hours. If you can’t stand to be at the golf course an extra half hour, why play? (People who carry on about how busy and time-crunched they are shouldn’t pick the most time-consuming games to play. Blitz chess takes only a few minutes, and so does a daily sprint at the track.)

It’s not as if you can’t do other things while a football game is on. I’ve trimmed hedges, cooked dinner, and even written stories without missing a single play. If the Alliance of American Football succeeds in churning-out 2+ hour games I’ll feel a little rushed watching them. High School games take 2 hours (sometimes less) and my biggest frustration covering the prep level is how there’s no time to think or reflect on whatever is happening on the field.

Thinking and reflection are not just luxuries but necessities to the successful sports bettor. She doesn’t mind the on-off-on-off rhythm of football. In fact, she’s glad it exists.

Why? Because it makes parlays a hell of a lot more fun.

The Most Fun Kind of Football Parlay

Betting basketball parlays can be entertaining if the games tip off at different times. But if the games overlap? Forget it. There’s nothing as ugly as losing 30 bucks in 3 minutes thanks to a pair of disappointing 4th quarters.

As for baseball, I’m against any wager that is likely to wind up in at least a single club you’ve taken the moneyline on being behind late in the ballgame. There’s nothing worse than the slow death of balls, strikes, and ground-outs when you’re trailing on the scoreboard.

But even an NFL parlay on a pair of midday Sunday games doesn’t give the viewer as much trauma.

The biggest plays in a football game can come at any time, but the likelihood of a pair of TD passes killing your parlay simultaneously is low. There’s time to breathe and calculate. Perhaps one of your picks is leading by 3 touchdowns and running out the clock, but another is going into the 3rd quarter with a deficit. That’s when you put the remote control down and focus all of your cheer-mojo on the potential comeback…while keeping tabs on the blowout that’s making you happy.

Watching Football

My favorite American football parlay is to pick a team that you know well to win a prime-time contest that you’re reasonably confident of the squad prevailing in, and then bolster the potential payout with some easy picks in the afternoon.

Under normal circumstances, a winning moneyline bet on Boise State to beat Fresno State will pay off 1-to-1 or 2-to-1 at the most. To up the ante, parlay the late-night pick with a bunch of heavy – and I mean heavy – moneyline favorites during the day. Then if Ohio State beats Minnesota and Alabama beats Ole Miss (both scant ML payoffs on their own), by the time the final game of the parlay rolls around, you’ve still got the same $ risk in the offing if Boise (or another west coast school) loses…but the payout on a final won pick (and subsequent winning parlay) can go sky-high.

Most Enjoyable Bet #2: Unders in Ice Hockey

It sounds strange to associate “Under” total-points bets of any kind with “fun.” After all, cheering for points is universally considered the most fun type of non-W/L outcome betting scenario.

But betting the low side of the O/U in ice hockey can actually eliminate one of the least-fun situations a sports gambler can be in – cheering for scoring chances in a slow-paced and tight hockey game.

They say baseball is a game of failure. But hockey takes the cake when it comes to failure. Attackers charge over the blue line over and over again with a very, very low probability of scoring a goal or an assist. Even if the team with the puck manages to get a sniper all alone in front of the goaltender, the goalie can make a great save…or the shot can simply be fanned-on.

Betting the Under in an NHL contest means that your desired outcome feels routine since hockey players routinely can’t score. It’s only the “extraordinary” circumstance of someone actually finding the net multiple times that can kill your wager.

A good tip is to look for goaltenders who have trouble stopping a few shots but get hot when faced with 40 or 50 shots. If a club is expected to take 40+ shots on goal against a lowly underdog, sometimes the goalie for the less-heralded team will end up in hog heaven, able to stay active and tuned-in for an entire 60 minutes or more. Meanwhile, a more evenly-matched opponent could put the GK in a situation where he faces fewer shots and is therefore less effective.

Some goaltenders struggle more than others with a low shots-against total. Familiarize yourself with the goalies who play their best against strong attacking teams that always have the puck.

Most Enjoyable Bet #3: Tournament Futures

We preview a lot of season-futures at, and fair play to the gamblers who go all-in on those markets. Those who followed my advice and took the L.A. Rams in preseason to prevail in Super Bowl LIII nearly got a 20-to-1 payoff out of it. Those who wagered on the Mountain Goats to win the NFC Championship did get a handsome payoff.

But tournament-title betting combines the best elements of single-game markets and futures markets. Especially in sports such as basketball, baseball, and ice hockey – competitions in which tourney schedules are not spread-out over months due to other club obligations the way that the UEFA Champions League and Nations League schedules are laid out.

March Madness is the time of year in which gamblers around the world pick a team and have a (round) ball cheering them on over a shotgun-format of only 2-3 weeks. But the NCAA Tournament (or the NIT Tournament) is not the only fun futures wager for impatient people.

Look at other tournaments at home and abroad for opportunities to root for “your” squad all the way to the final. The IIHF World Championships and World Junior Championships are extremely fast-moving and fun betting brackets. Golf and tennis futures bet also tend to pay off (or lose) quickly, at least compared to that wager you already made on the Boston Red Sox to reach the Fall Classic in 2019.

Most Enjoyable Bet #4: Betting Against “Reputation” Props

Proposition markets are unique in the sense that gamblers have already chosen “fun over systems” when they peruse the lines. Just the notion of betting on silly Super Bowl or March Madness props (such as whether the captain of the winning team will say “God,” “Mom” or “Coach” first in the post-championship game interview) can betray a betting public consumed with pleasure and a bookie all-too happy to take their foolishly-gambled money.

But wait. There’s actual betting value in the right kind of prop market…and unlike the search for “value” in other markets, out-foxing a bookie on a prop is pretty much always a blast.

In midst of the 2018-19 NBA basketball season, DeMarcus “Boogie” Cousins returned from injury to play his first game with the Golden State Warriors alongside an All-Star starting lineup of Stephen Curry, Klay Thompson, Kevin Durant, and Draymond Green. The opposing L.A. Clippers are a decent scoring team who can sometimes struggle to stop big men in the paint. Since Cousins is the definition of an effective big man, and since Curry had gone bananas with record-book shooting performances prior to the Warrior-Clipper tip off, the Over/Under point total and various prop bets for Boogie’s debut became inflated and sat too high at various betting sites.

Boy, did I have fun taking the low side of those props. I cleaned up on Boogie scoring less than expected, other Golden State superstars to shoot less accurately than expected, and of course the Over/Under line once the total was posted closer to 250 points than 200.

Fundamental truisms in sport exist whether or not the athletes are famous and highly-touted. The Warriors were playing their very first game with a new lineup, featuring a player who had recently healed well-enough to practice. Of course they weren’t going to score 150 points! But that sounds like mere 20-20 hindsight to the bettors who bought into the hype that a “super-team” would immediately start killing-off the entire NBA. I love the Warriors as a futures pick to win another title this summer…but they’re human beings like the rest of us.

Most Enjoyable Bet #5: Massive Underdogs on the Moneyline (or ATS)

Finally, there’s the time-honored “long shot” wager – picking a heavy underdog to beat a prohibitive favorite straight-up. Those who took AFC Wimbledon to beat West Ham in the 2018-19 FA Cup tournament were probably as jubilant after the match as Wombles supporters themselves.

The only problem is that in certain sports, online betting sites choose not to offer moneyline wagers on the biggest expected mismatches. Why should they? If the bookmaker puts out a line for some mid-major school to beat Alabama on the gridiron, and it happens, then the site is paying out all kinds of money. But if Alabama wins, there’s very little for the house to collect even as they’re not paying out very much of a % on the won ML wagers.

That doesn’t mean you can’t have fun betting on a big-time gridiron underdog, though.

One of my favorite bets paid off when eventual College Football Playoff champion Clemson hosted Georgia Southern early in the 2018-19 season. Dabo Swinney’s Tigers were almost 40-point favorites on the point spread against a GaSo team from the Sun Belt, a conference that can’t garner a 3rd of the TV rating of games in Clemson’s ACC.

But a tropical depression was enveloping the entire state of South Carolina at the time, and I knew that Georgia Southern had a chance to play well on defense and at least grind out some 1st downs with the Eagles’ shotgun-option attack. A distracted Clemson team – making plans to scurry off campus as soon as the rainy game concluded – was likely to fall short of the 55-7 kind of win that bookies and the betting public expected.

Final score: Clemson 38, GaSo 7, and a win for the Eagles against the spread.

Betting a gigantic point-spread underdog (in football or basketball or other sports) can turn into great fun by subverting the usual frustration of betting the favorite to cover. Picking Clemson to whip Pittsburgh by 30+ points is terrific when it pays off, but it’s sort of like that SEGA game “Great Football” from the 1990s, where you only played offense and had to overcome a 28-point deficit before the video game’s timer ran out.

By contrast, the big underdog ATS presents a simple scenario – if it’s any kind of a good game, you win your bet.

And if you see your (+35) underdog-to-cover pick actually beat a titanic program straight-up? Don’t fret about not having taken the moneyline…because there probably wasn’t one.

Claim My $250 Bonus at Bovada!