15 Songs That Are Totally Worth the Gamble | Playlist 🎧

1. Ryan Beatty, “Casino”

Dreaming of David • Boy in Jeans / Mad Love / Interscope • 2020

“Come around like the moon, sun / Most of the time you’re on my mind.” Ryan Beatty writes amazing songs about boys, period.  Both his 2018 debut album, Boy in Jeans, and hs sophomore album, Dreaming of David, support that assertion. “Casino”, a highlight and single from the project, fits the bet-making, card-playing, gambling sentiment of this list!

“Casino,” which runs north of four minutes is written and produced by Austin Anderson, Daniel Fox, Happy Perez, and of course, Beatty.  The production is a contrast from previous songs from Beatty, opting for accompaniment from rhythmic acoustic guitars. As always, he shines vocally.  He sounds quite expressive, with lovely falsetto exhibited on the pre-chorus (“Hood on, hand in my pocket, walk away”).  Besides awesome lead vocals, there are also some gorgeous vocal harmonies on the pre-chorus as well as on the bridge section, where the opening quote of this review hails from.  While the pre-chorus is characterized by falsetto, Beatty switches to full-fledged, dynamic chest voice on the memorable, repetitive chorus: “Love me to death or don’t give me anything / Oh yeah, oh yeah.”

Throughout, “Casino” features a number of interesting lyrics that find Beatty reflecting on love.  On the first verse, he sings, “The oxygen was choking like death grips around me / I even thought I couldn’t be sadder than that, I am.” Later, he’s perturbed about his lover’s song being played.  Despite the misfortune, he asserts, “I sing along and laugh just in case of the opposite…/ Everything was blurry so I couldn’t see, thankfully…” Stylistically, Beatty is somewhere between pop and R&B, so there’s a broad appeal.  Pardon my French (or lack thereof) but Ryan Beatty is the shit, and so is “Casino.”

2. Motörhead, “Ace of Spades”

Ace of Spades • Sanctuary • 1980

“If you like to gamble, I tell you I’m your man / You win some, lose some, it’s all the same to me…” If you were a skateboard video game enthusiast like me, you were totally into the Tony Hawk Pro Skater series.  The soundtrack to the series was always dope, featuring classic hip-hop and classic rock. One my very, very favorite songs that was highlighted by Tony Hawk Pro Skater 4 (showing my age, of course), was “Ace of Spades” by English rock band, Motörhead.

“Ace of Spades” is undoubtedly the most popular and renowned song by the late great Lemmy and company. Serving as the title track from the 1980 album Ace of Spades, the song rocks hard AF.  Lemmy delivers assertive, gritty vocals, supported by an enthusiastic, rollicking musical backdrop by the band (including his bass playing). While the card referencing title was enough to secure “Ace of Spades” a spot on this list, the lyrics also reflect the theme.

“You know I’m born to lose, and gambling’s for fools
But that’s the way I like it baby, I don’t wanna live forever
And don’t forget the joker.”

3. Sech, “Casino”

1 of 1 • Rich Music Inc • 2020

“Tú eres como el casino / A veces gano pero casi no / Sabiendo que to’ el tiempo pierdo / Siempre que puedo vuelvo, yeah.” What exactly is Panamanian singer Sech singing on the chorus of “Casino?” Well, here’s a rough translation of the chorus from Spanish to English:

“You are like the casino
Sometimes I win but hardly
Knowing that I waste time
Whenever I can I come back, yeah.” 

Basically, he compares her to a casino, which is a risky place because you take a chance on losing.  Sech goes on to say he often loses, where her affection is concerned, yet keeps on trying despite wasting his time.  Ultimate, this smooth gem from 1 of 1 (2020) has nothing to do with a real casino, though it’s a song that is TOTALLY WORTH THE GAMBLE.

4. Leon Bridges, “Bet Ain’t Worth the Hand”

Good Thing • Columbia • 2018

“I might regret that I can’t be your man / Sometimes the bet isn’t worth the hand / And I can’t keep lettin’ this wave carry me away…” Talented, Grammy-winning retro-soul artist Leon Bridges easily secures a spot on this bet-driven list with “Bet Ain’t Worth the Hand”.  “Bet Ain’t Worth the Hand” appears on Bridges fine, 2018 sophomore album, Good Thing.  Soul enthusiasts will feel like they returned to their heyday listening to the record. The old-school shtick is alive, with harp arpeggios, glockenspiel, strings, and an overall lush backdrop.  Safe to say, the production is perfect fuel for Bridges’ fire, whether he needed the extra spark or not.

Bridges definitely sounds confident and mature on “Bet Ain’t Worth the Hand.”  The falsetto is formidable, while chest voice is incredibly commanding and emotional. Adding to the jubilance is the solid songwriting with an undeniably prudent message.  Short and sweet, “Bet Ain’t Worth the Hand” just crosses the three-minute mark. Leon is in top-notch form.  How much does the song have to do with cards? Little, but like, love, or otherwise can always be a gamble.

5. Sleepy Hallow, “Bankroll”

Sleepy Hallow Presents: Sleepy for President • Winners Circle Entertainment • 2020

What is a bankroll – that is the question! According to Merriam-Webster, it’s simply a “Supply of money.” According to European Gaming,  “The bankroll is the money that a punter has set aside specifically for gambling.” Okay.  Let’s consult one last outside source – Urban Dictionary! According to the ever-reliable UD, a bankroll is “an amount of money a poker player has available to him/her.”  So, with three sources telling us exactly what a bankroll is, let’s consult Sleepy Hallow, shall we?

“Bankroll” by the Brooklyn rapper, appears on his 2020 mixtape, Sleepy Hallow for President.  Sleepy Hallow keeps things short and sweet, as “Bankroll” runs around 2:15 in length.  On the Great John and 2300 produced number, Hallow is all about the flex.  That flex action encompasses money, first and foremost, as well as women.  The chorus sums things up perfectly:

“Tryna watch that money grow
You know my heart cold, ain’t no way you gettin’ close
I just got a bankroll, ‘roll, ‘roll, ‘roll, ‘roll
Gotta make sure mama good ‘fore I get my chain froze
Trappin’ out the same clothes
Now tell me who had us when we ain’t had nowhere to go?”

Also, the never tiresome tale of the come up is referenced as well.  But it’s not all rosy, with lines like “I do drugs for the pain and I think it’s workin’…” That’s definitely questionable Sleepy Hallow…

6. Lady Gaga, “Poker Face”

The Fame Monster (Deluxe) • Interscope • 2009

“Love game intuition, play the cards with spades to start / And after he’s been hooked, I’ll play the one that’s on his heart.” Listening to “Poker Face” without context, or playing extremely close attention to the lyrics, it would seem that it’s a harmless, dance-pop record by Lady Gaga. Dance-pop often focuses on the production and vibe more so than the lyrics, so, Lady Gaga could easily get a bit of a pass given the infectious, killer vibes of “Poker Face.” Don’t let the infectiousness of this number one hit from The Fame Monster fool you.  Basically, you should totally ‘read into’ the chorus, which clearly insinuates bisexuality, confirmed by the musician herself.

There’s nothing wrong with that, but back when, how many caught what Gaga was singing about?

“Can’t read my, can’t read my
No, he can’t read my poker face
(She’s got me like nobody)
Can’t read my, can’t read my
No, he can’t read my poker face
(She’s got me like nobody).”

“Poker Face” previously appeared on 13 Songs That Focus on the Face, 12 Interesting Songs That Reference Bisexuality, and A Compendium Comprised of 100 Notable LGBTQ+ Songs.

7. Rihanna, “Russian Roulette”

Rated R • The Island Def Jam Music Group • 2009

Let’s investigate! Roulette, defined by Merriam-Webster, is “a gambling game in which players bet on which compartment of a revolving wheel a small ball will come rest in.” Interesting! European Gaming has a similar description, with a few more details.  A simpler, non-gambling associated definition simply plays out as follows: “Something involving a high degree of chance and unpredictability.” Basically, roulette is quite the GAMBLE, and this list is all about GAMBLING!  Back in 2009, Rihanna served up the perfect gambling centric number.

“Russian Roulette” is one of my all-time favorite Rihanna songs from one of my all-time favorite albums by the artist (Rated R, 2009).  Rated R remains the darkest Rihanna album to date, marking a more adult, mature artist.  “Being a ‘fucking lady’ was the mantra” of the project, per Def Jam. The album, of course, followed her infamous relationship with Chris Brown, notably the abuse.  Why mention this? Well, many consider “Russian Roulette” to reflect her experience in a sketchy relationship.  The lyrics are chilling throughout, not to mention how she chooses to sing them.

“Take a gun and count to three
I’m sweating now, moving slow
No time to think, my turn to go.”

Of course, the centerpiece is the chorus, which is the most expressive and emotional part of the song:

“And you can see my heart beating
You can see it through my chest
Said I’m terrified, but I’m not leaving
I know that I must pass this test
So, just pull the trigger (Trigger, trigger, trigger).”

8. RMR, “DEALER”

Ft. Future & Lil Baby

DRUG DEALING IS A LOST ART • CMNTY CULTURE / Warner • 2020 

DRUG DEALING IS A LOST ART – what a f🤬🤬king album title. Naturally, before ever hearing “DEALER,” it locks in what rapper RMR is going for: drug dealing.  When it comes to gambling, per European Gaming, “The DEALER [is] an employee of the casino that is responsible for dealing cards to players and controlling the general flow of the game.” Compare that to the job of a drug dealer – a plug – and there are definitely similarities.  Sure, a drug dealer isn’t controlling baccarat, blackjack, or poker as European Gaming suggests, but they are dealing out various drugs…

On the remix of the song, RMR taps Future and Lil Baby, two of trap music’s biggest staars.  RMR kicks things off, focused on drug use and, shocking, bitches.  “Percocet pills, my nigga / Can’t stop fuckin’ round with ‘em,” he sings in mellow fashion on the chorus, continuing, “Pop a Xan, gon’ sip a Tech with it / Codeine got me in my feelings.” He goes on to commence his verse with the statement, “I’m high now.” Future matches the sentiments of RMR on the second verse, where he’s “Fuckin’ on your bitch, throwed up” and “Crushin’ X oon your punani…” Wow! As for Lil Baby, on the third verse, he kicks things off classily: “What’s your choice of drug? / I be sippin’ syrup, think I’m in love, woah.”

9. Miguel, “Deal”

Wildheart • RCA • 2015

“Love me, love me for profit, I can make you go down / I can show you the money if you wanna go out.” “DEAL” is one of many highlights from Wildheart, the third studio album by Grammy-winning R&B artist, Miguel.  He enlists his younger brother, Nonchalant Savant, for the assist. “DEAL” features an infectious groove that instantly latches. Ultimately, the record represents alternative R&B at its finest.

So, what’s the ‘deal’ with “DEAL.” Basically, the ‘deal’ is about securing sex by flaunting drip, money. I wouldn’t go so far as to say prostitution, but the prospective ladies will certainly get benefits it seems.  The chorus is simple, but definitely scintillating chorus:

“Want money? Got clout
Need bitches, need bitches
Give it, babe.” 

10. Marilyn Manson, “Odds of Even”

The Pale Emperor • Loma Vista • 2015

“Odds of Even” concludes one – if not – the blackest album of 2015.  That album would be The Pale Emperor, courtesy of The Antichrist Superstar himself, Marilyn Manson.  “Odds of Even” is one of many great songs on the hellish project, though it’s eclipsed by the likes of “Killing Strangers” and “Third Day of a Seven Day Binge.” The reason why “Odds of Even” earns a spot on 15 SONGS THAT ARE TOTALLY WORTH THE GAMBLE is thanks to its reference of odds, which are key to betting.  “Odds of Even” is definitely worth the gamble… at least the song itself.

“This is the house of death / Where even angels die in arms of demons…” Disturbing… Fittingly, Manson saves one of the creepiest songs for the end, where his frightening voice sings at the end, “No one is exempt from the odds of even.” It is what it is and that’s very black.  Manson makes a very deep statement, that can be interpreted a number of ways.  In a sporting event, even odds in a point spread means that either team or athlete has an equal chance at winning the game because there’s no decided advantage to sway things one way or the other.  Manson seems to suggest that the ODDS to get EVEN are null or the odds to escape death is impossible, insurmountable, etc.  Regardless what you think of Manson, he has a point on this one.

11. Aminé, “BLACKJACK”

ONEPOINTFIVE • Republic • 2018

If you’ve never played Blackjack, well, you’re totally missing out! I’m not card game expert, but Blackjack is one that I’ve enjoyed a few times during my lifetime.  According to European Gaming – especially for those naïve of the game – “Blackjack is a table game where players try to beat the dealer by getting a hand closer to 21 points without exceeding.” Pretty simple, right? Right!

Now that you understand what Blackjack is, know that the Aminé song, “BLACKJACK,” from ONEPOINTFIVE (2018) has nothing to do with the card game.  How often does the “Caroline” rapper mention 21? None.  How often does he reference an Ace? None.  Honestly, was does “31 hoes in my Facetime” have to do with Blackjack? What does Jack Black have to do with Blackjack?  Honestly, the Jack Black references, plus the fact this is a short but sweet banger make it TOTALLY WORTH THE GAMBLE.

“Rockin’ and rollin’ like Jack Black (Yoo)
Schoolin’ you niggas like Jack Black (Yah)
How could you not like Jack Black? (How?)
I put that on my mama nigga, no cap (Huh).”

12. Bilal, “Winning Hand”

A Love Surreal • Entertainment One Music • 2013

There is nothing like scoring a winning hand.  It’s a heavenly experience, like sex… or not.  Okay… awkward… Anyways, on A Love Surreal, the 2013 album by Bilal, the song “Winning Hand” is nothing short of elite.  “Winning Hand” is highlighted by clever songwriting, first and foremost.  Beyond the songwriting, the record features some of the album’s strongest ‘neo-soul’ style production.  Add in those soulful pipes by the Grammy-winner and you have nothing short of a winning hand.

The key lyric that solidifies the card-playing, potential gambling aspect of “Winning Hand” actually comes in response to love and romance. Bilal praises and charms his girl in lofty fashion, comparing her love to a strong performance:

“A game change, I’m on the roll
Dealer, hit me again
Yeah, we’re winning again, I’m on the roll...”

Keeping things compelling, things switch-up on the third verse of the song – or however you best wish to characterize the section. “I’m on a roll, on a roll… / You came relunctantly… / I’ve had to bring it out you / So shine, when you want to be / Girl it’s ok to cry and laugh at the same time…” Again, the big takeaway is that “Winning Hand” is indeed a winning hand for Bilal as well as the listeners.

13. Keyshia Cole, “Playa Cardz Right”

Ft. 2Pac

A Different Me • Geffen • 2008

A Different Me is a great Keyshia Cole album, period. However, the 2008 LP doesn’t have the same buzz as her debut, The Way It Is, or the tour de force that precedes it, Just Like You. Even though it lacked a big hit, A Different Me had some solid singles including “Playa Cardz Right” featuring 2Pac.  Obviously, 2Pac had long been deceased when “Playa Cardz Right” was released as a single, but, it’s one of those rare posthumous singles that actually ends up being a success.

In gambling, it’s definitely important to play your cards right, or your ass is going to be broke.  In this case, 2Pac and Keyshia Cole suggest taking things slowly but surely to attain a healthy relationship.  Cole makes it crystal clear on the chorus what she wants to be to her man:

“I wanna be the one who
Who you can depend on who
Who be the one who be there
Through the thick and thin
Go by the water we will
Be there ‘til the morning
We won’t leave until the night
And we will be forever more.”

“Playa Cardz Right” is just a rock, solid hip-hop/R&B joint. Smooth, sexy, and incredibly sensible in its messaging.  You better “playa cardz right!”

14. Radiohead, “House of Cards”

In Rainbows • XL Recordings • 2007

“The infrastructure will collapse / From voltage spikes / Throw your keys in the bowl / Kiss your husband ‘good night.’” One way to describe darling alternative band Radiohead is heady.  Are Thom Yorke and company ‘heady’ on “House of Cards” (In Rainbows)? Yes, expectedly. That said, Yorke – or his character in the context of the song – clearly states he wants to be in a relationship with a married woman: “Forget about your house of cards / And I’ll do mine.”

Even though there’s an obvious narrative constructed here, “House of Cards” certainly isn’t closed to multiple ideas and interpretations beyond its basic plot. Often, when ‘house of cards’ is referenced, well, we expect things to totally crumble, no matter how specific the scenario. In the context of gambling, well, the gamble is stacking up those cards and hoping one card doesn’t demolish the whole house. “House of Cards” previously appeared on 14 House Songs More Thrilling Than Chilling at the House, one of the ‘OG’ The Musical Hype playlists.

15. Kenny Rogers, “The Gambler”

The Gambler • Capitol Nashville • 1978

You can’t have a gamble-centered playlist without having the Kenny Rogers classic, “The Gambler.” “The Gambler” marked the late country singer’s second Grammy win, earning honors for Best Country Vocal Performance, Male in 1980.  “The Gambler” was also nominated for Record of the Year, while the parent album, The Gambler, was nominated for Album of the Year.

The chorus, the centerpiece of “The Gambler,” perfectly captures gambling, as it should:

“You got to know when to hold ‘em, know when to fold ‘em
Know when to walk away and know when to run
You never count your money when you’re sittin’ at the table
There’ll be time enough for countin’ when the dealing’s done.”

The chorus, of course, also provides pretty good life advice, if you ask me.  Of course, the verses are quite colorful, telling a story in only the manner a great country song can.  I’ll leave you with the fourth verse, which fits right into the gambling theme of this list and confirms exactly why this classic is a song TOTALLY WORTH THE GAMBLE!

“Every gambler knows that the secret to survivin’
Is knowin’ what to throw away and knowng what to keep
‘Cause every hand’s a winner and every hand’s a loser
And the best that you can hope for is to die in your sleep.”

FACTS!