Caskey On His Cult Fanbase, Dropping $100 Mixtapes, Birdman, Jelly Roll, Yelawolf, “I’m A Virgin”

Caskey "Off The Porch" Interview
We recently sat down with Caskey for an exclusive “Off The Porch” interview! During our conversation he talked about the Orlando music scene exploding since he first started rapping, building up a cult fanbase, being vulnerable in his music, making music being therapeutic for him, jobs he worked before he signed with Cash Money Records, fans telling him how his music helped them, liking that his music can take him back to dark places during his life, his close relationship with his mother, his new album ‘Cadillac Music’, working on the album for 8 months, his single “I’m A Virgin”, taking a different approach for his music videos now, reveals what Birdman is really like, the inspiration for his $100 mixtapes, his fans not leaking the first tape online, his thoughts on how little that streaming pays out, touring with Yelawolf, their close friendship, their upcoming collab project, reveals that Jelly Roll was the first artist he worked with, paying him $250 for a feature, building a close friendship with Jelly, goals for 2024, and much more!
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Interview by Haze
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DGB Media
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"Off The Porch" is Dirty Glove Bastard's exclusive interview series where artists, producers, DJs & industry insiders are given a platform to tell their unfiltered story. Dirty Glove Bastard was created in 2007 to shine more light on the buzzing, regional music scenes in the South & Midwest.
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[@caskey407]

great interview and i appreciate yall giving artists a platform to speak on. keep killing it nothing but support from my end

[@jakefromtulsa6894]

Love from Tulsa homie

[@sonnyrydgren]

This is great! Keep grinding bro!

[@beatsbythekilo]

Salute from South Philly

[@slcgenerallee]

So glad they put you on bro!! You're music has changed the Lee family for the better! Never stop Cas! I love this man like a brother and i have only met him a handful of times. Most genuine dude you will ever meet! Love you bro!🤞🦍💜

[@kevodean]

this fucking interview resonates with me on a another level, I too was big in the underground music scene in fl back in the early 2000s and i actually have friends that were "business associates" of caskey and his group of friends from back then. My cousin got picked up at a early age by Neyo and taken under his wing, this was back in probably 2008 or so, anyways its crazy how so many of us who grew up in FL have gone thru similar trials and tribulations at an early age and it sent so many of us down the path of abusing drugs and other addictions

[@killz954]

It’s an honor to have you represent Florida bro. You’re the epitome 💯 your music & character is highly appreciated, respected & inspirational

[@SethEST19XX]

I know Caskey doesn’t do a lot of interviews but when he does they’re always so good. 🙏🏻

[@pookpmm]

I just discovered him and im hooked. Great dude

[@Powerwalker73]

Me too! He is the BEST!!! I’m hooked 👍🏽

[@Tyler-nhoodgremlins]

Sheesh you got alot to catch up on!! The blacksheep been killing this shit

[@pookpmm]

@Tyler-nhoodgremlins you right! I think his freestyle his did back stage on his tour is my favorite. The part about Birdman, Wayne, and them was some of the realest stuff I've ever heard. And you can actually hear every word he says which is rare these days😂

[@RadDadMoody]

Finally somebody with substance on this porch!

[@TheAndrewforbes88]

Love Caskey, what a great interview!

[@SonicPimpTX]

Dude I love Your authenticity. The honesty You keep in all your music and conversations really resonates with people. Thank You for being Yourself. Loving Your work Homie. I respect the path you have taken, and where you ended up. Mad respect, and good on You for being a family Man despite all the distractions You could have given yourself

[@KMT420ART]

I’ve been on stage with this man. He is such an energy and pure soul!!! So proud of his sobriety!!! He spoke life into me and everyone around

[@dragoti1122]

I always look forward to your interviews or videos…they’re intense. 🔥❤️❤️

[@MarcelCox2-ir4wj]

CASKEY you are lucky to have a mother I have no family left except this one ... Family and music are everything to me it's not about the money I will spit this shit till I'm six feet deep ... You guys push me to want to be a better artist and person I learned to vent shit on the mic and use the negatives and turn them to something beautiful art

[@aleahhaven7323]

What’s ur name? I’ll look you up give u chance if ur good u got a supporter here

[@user-fq8sg9of9p]

I’m surprised to see bro even took them up on an interview he don’t do this much at all humble dude fashoo 🔥🔥🔥🔥

[@BradLopez-jq3bf]

Na fr he really don’t bro is super humble and doesn’t do much shyt like this at all shows this platform is different from the rest for sure!

[@andreahuffman8227]

I love your authenticity 🔥❤️👑

[@purpsfortnitecontent1338]

@caskey407 your music is so raw and real. Roanoke virginia show was lit in the rain

[@koreyvisage]

Reading that letter was personal too 💪🏻

[@randomland9088]

I love how humble he was when he said "I don't ever think I was the best" His lyrical skill has come a long way, I used to think this man was corny tbh. He worked his fkn ass off for this..

[@robertnorris7547]

Caskey the G.O.A.T. Caskey your just one good dude. You are by far my favorite artist. Come back to Seattle so we can chop it up again. .

[@trapaton6824]

This the one I been waiting on Florida shit💪🏾

[@kira-cm5bo]

Thank you so so much for this and for your careful thought in how you talk about stuff here. Awesome

[@joshuamichaelcook1987]

caskey is the man !! motivation at its finest !! the hustle is real !! to a dope 2024 !!

[@chrischrisson7921]

love this guy

[@LidoBombs2]

THE LEGEND

[@sitstill1561]

Caskey fire interview

[@VUDUDRU]

Dope

[@CreativeFreedomUniverse]

Love caskey. Great interview!

[@ONLYONETWO]

Run it up bro!

[@aarongraham214]

Been a fan since day 1. I tell everyone about caskey. Under rated. Top 5 white rappers out and top 10 rappers/ music makers in the game. Much props. Keep on black sheepin it..

[@robertnorris7547]

Same it been so awesome watching him grow. He's so underrated. I wish em would make some music 🎶

[@kreativeenergy4847]

You good in Texas with Cadillac 🤘🏿💯👑

[@BradLopez-jq3bf]

🐐🐐🐐🐐🐐

[@jimmyskoog]

Amazing interview bro. Much love from Sweden 🇸🇪

[@MichaelCobbs]

Good interview.

[@tytheriot3388]

The journey as a whole

[@tallyupproductions1463]

this man is a legend in FLA for over a decade!! Otown!!

[@tytheriot3388]

Everything leads up to that one moment that changes everything

[@lilwikka]

legend

[@johns3040]

That first 💯 album 🔥. Waiting on the 2nd one to hit the mail. 💪 Caskey 🔥.

[@babyjesus2025]

Never heard his music but its Refreshing to see somebody real about who they are... Love From new orleans....

[@robertnorris7547]

Bro you need to he's dope.

[@stevenharper2249]

Solid interview 💯

[@mikeyb3861]

Love his music

[@tytheriot3388]

So many people relate to being blacksheeps in their own lifes and waves

[@roddollaz]

I've been a fan since 2013 when I first seen his videos on World Star Hip Hop #PureMotivation 💯

[@BLVCKSH33P_AK97]

LIVING LEGEND!

[@viiibe5318]

💎 Jewels 💎

[@cswadventures7229]

Caskey 🐐

[@KoyotePenny_2024]

Great interview though.

[@user-mn9tf5nr3t]

AWESOMENESS 🎉🎉🎉🎉🎉

[@47Mufasa]

goat

[@kira-cm5bo]

"Rigged this thing to just hang" omg.

[@Hobohunter23]

Caskey is a good fucking dude! Wish you showed some of the interviewer asking questions, kinda seems like a casting couch haha... good shit though, I'm unfamiliar with this channel so maybe it's just me

[@kira-cm5bo]

"I've been real transparent." Lmao 😂❤

[@brandonkessler1357]

Dudes awesome! Wish him the best in his endeavors 💯😎

[@StevenSCott-ir6nn]

❤❤❤

[@natanigallegos4142]

This bro is the poster child of "When I grow up I'm going to be a rapper".

[@kira-cm5bo]

100 ❤

[@mattwilcox1884]

If you ain’t heard of the black sheep then you ain’t a real hip hop fan

[@user-ys1cw3sv4n]

Black Sheep 4L 💙

[@RashawnCoward]

My city getting over look for year's my g...S.T.A.N.D. UP?$!804💯🙈🙉🙊🤑💣

[@tytheriot3388]

Dawg i listen to your music eryday.shits dope..and ima o.g. 50yrs old.crazy lifestyle,but last 6 yrs been great.got married 2nd time.this is my take off time tho..stay reall

[@DaBlazinKid]

Shout to Caskey for always killing it. The corny Vlad style interview setup gotta go though

[@MarcelCox2-ir4wj]

I know what's missing on black sheep 2 me ....

[@DaRza17]

I love how hes not tryin to act "black" I hate when ppl do that.

[@Phoenix_Atlas]

I thought he was from Chicago

[@jamesharris6414]

Haters in the comments be so jealous of this dude 😂

[@drptp5017]

Cashmoney always do right for the white man. But for the black man always wanna do the brotha bad

[@joshuabutler999]

Dennis Rodman

[@calvinmartin3413]

Drake...

[@Harleen_Quinzel_PhD]

You copied me. #tribute

[@KoyotePenny_2024]

Who r u anyway? No respect 4 u after i seen u try to attack Burden who the hell r you that wasnt cool or nice. Im just being aurhentic 😂😂😂😂😂

[@Rohzez]

This Is Way Too Slept On 🥱💎

[@richardsagan9448]

You still with birdman?

[@XtremePot420]

No, he’s Independent now. Black Sheep Records 😏

[@gmanvalenzuela1875]

Independent keep pushing entertainment black sheep records.

[@PRODGAL304]

@caskey407 Respect bro your music help me thru some rough times and i love how you express yourself in other ways with art, fashion, poetry. True artistry

[@7HEdon777]

One of the most overrated rappers in history..... Dude is hardly decent, much less great.... 😂😂🤦🏼‍♂️🤦🏼‍♂️

[@PierreGoodforwin]

❤❤❤

[@shahaneperera349]

❤❤❤