| 301. | Sad Boy Radio LXXXVII: Never Thought I'd Be Here? ( W/ Sketchy Frankie) | 11 | Show |
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| 302. | Sad Boy Radio XLIX: Somebody That I Used To Know? (W/ Hayward of KNVS) | 11 | Show |
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| 303. | “The right people love you through ugly & good” #podcast #mentalhealth #music | 11 | |
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| 304. | Sad Boy Radio LVIII: Am I Good Enough? (W/ Stevensjpeg) | 11 | |
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| 305. | “You have to learn from your L’s, not quit because of them” #bigsean #podcast #music #chicago #latin | 11 | Show |
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| 306. | “Your SOUL MATE is gonna bring you complete peace" #podcast #mentalhealth #music | 11 | Show |
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| 307. | Sad Boy Radio C: I'm Only Human? (W/ DJ SIMMY) | 11 | Show |
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| 308. | “You lose your identity trying to be liked on social media” #podcast #mentalhealth #music | 11 | |
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| 309. | Sad Boy Radio CXXXII: Now That You're Gone? (Senite Interview) | 12 | |
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| 310. | “I still get nervous when I DJ” #dj #chicago #badbunny #reggaeton #podcast #music #hiphop #ozuna | 10 | Show |
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| 311. | Sad Boy Radio LV: I'm Hurting, But What's Art Without Pain? (W/ Baka of KNVS) | 10 | |
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| 312. | “There isn’t a journey that’s steady, life is about valleys & peaks” #podcast #mentalhealth #music | 11 | Show |
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| 313. | Sad Boy Radio XLV: Never Satisfied With Life? (W/ Nico Supremo) | 10 | |
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| 314. | Sad Boy Radio LXVIII: It'll Be Okay Someday? (W/ GloUp Jake of Lyrical Lemonade) | 10 | Show |
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| 315. | “Work has become your priority rather than building a relationship” #podcast #music #mentalhealth | 10 | Show |
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| 316. | Sad Boy Radio XXXII: Something is Always Missing? | 10 | |
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| 317. | “I wanna help people realize their dreams early” #music #jcole #podcast #chicago #pvtstck #latino | 10 | Show |
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| 318. | “I’m split between the responsible & irresponsible me because of my culture" #podcast #mentalhealth | 11 | |
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| 319. | Sad Boy Radio IX: True to Self? | 10 | |
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| 320. | Sad Boy Radio II: What Made You This Way? | 10 | |
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| 321. | “Your subconscious learns to reject when all you’ve been told is ‘no’” #podcast #mentalhealth #music | 37 | Show |
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| 322. | “You can love a person, but express it to them in ways they don’t feel it…” #podcast #music #love | 10 | Show |
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| 323. | Sad Boy Radio XLIII: I'm ENTLD To Be Happy? (W/ AK of ENTLD) | 10 | Show |
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| 324. | Sad Boy Radio VII: The Drugs Are Talking & No One is Listening? | 10 | |
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| 325. | Sad Boy Radio IV: Toxic Relationships? | 10 | |
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| 326. | Sad Boy Radio LXXVI: For This Life I Cannot Change? (W/ Dre Wicked) | 10 | |
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| 327. | “Where I’m from forced us to over analyze & take extra precautions for protection” #jayz #podcast | 10 | Show |
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| 328. | Sad Boy Radio XXXVII: Can I Count On You? (Dropping Gems) [W/ TFK Co-Founder Allen The Official] | 9 | |
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| 329. | Sad Boy Radio: Am I The The Broken One? (W/ BeatsByLexx) | 9 | |
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| 330. | “I was waiting for people to own up to their mistakes for too long” #podcast #mentalhealth #music | 20 | |
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| 331. | Sad Boy Radio III: Who Am I? | 9 | |
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| 332. | “I NEED your support RIGHT NOW, not 3 years from now" #podcast #mentalhealth #music | 9 | |
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| 333. | Sad Boy Radio VIII: Remember Me? | 9 | |
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| 334. | “The only person that holds you back is yourself” #music #podcast #kanyewest #creative #chicago | 9 | Show |
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| 335. | Sad Boy Radio XLVI: When I See You Again? (W/ Isa) | 9 | Show |
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| 336. | Sad Boy Radio CXXII: What Does Love Look Like? (theMIND Interview) | 9 | |
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| 337. | “Every man lives two lives, and his second one starts when he realizes you only live once” | 9 | |
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| 338. | Sad Boy Radio XCIV: Hasta El Fin (W/ DJ Fredy Fresco) | 9 | Show |
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| 339. | “The Bible is a manual that you can apply to modern day” #bible #podcast #justinbieber #religion | 9 | Show |
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| 340. | “Nobody thinks about anybody but themselves” #podcast #music #mentalhealth | 9 | Show |
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| 341. | We hold onto times in our lives we didn’t cherish when we lived them #podcast #music #mentalhealth | 9 | Show |
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| 342. | “Those bad days will pass" #podcast #mentalhealth #music | 9 | Show |
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| 343. | “You grow up & suddenly you have to worry about more than the small stuff” #podcast #mentalhealth | 9 | Show |
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| 344. | Sad Boy Radio XL: What Is Happiness? (W/ Ceasedays) | 9 | Show |
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| 345. | “Anybody that puts their mind to something can do it” #podcast #mentalhealth #music | 9 | Show |
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| 346. | Sad Boy Radio XCVIII: Hoping To Be Okay? (W/ Danielle Casel of No More Heroes) | 9 | Show | No More Heroes
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| 347. | “I WISH everything we worked towards, had worked out” #podcast #mentalhealth #music | 10 | Show |
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| 348. | Sad Boy Radio V: Does Time Heal All Wounds? | 8 | |
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| 349. | “Anything that I want to do, I manifest it” #podcast #mentalhealth #music | 8 | Show |
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| 350. | OG Juwon Interview: Being SENT to Nigeria, OG Music Group, Purpose in Life & MORE | Sad Boy Radio | 12 | Show |
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| 351. | Sad Boy Radio XXI: Thank you? | 8 | |
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| 352. | “NEXT TIME I SEE BRON HE FOOD” #podcast #mentalhealth #nba | 23 | Show |
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| 353. | “Life isn’t guaranteed everyday, don’t compromise it” #podcast #mentalhealth #music | 8 | |
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| 354. | Sad Boy Radio XI: Letter to My Grandmas? (Cherish Those Around You) | 8 | |
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| 355. | FEMDOT PERFORMING “2003”#podcast #perform #live #femdot #music #hiphop #chicago | 8 | Show |
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| 356. | Sad Boy Radio: ONE YEAR? (W/ SBR MVT) | 8 | Show |
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| 357. | “People only take a small portion of what they see online” #podcast #losdsvlds #macmiller #problems | 8 | Show |
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| 358. | “We’re still living in toxic cycles rather than breaking them" #podcast #mentalhealth #music | 9 | |
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| 359. | “Happiness is easily replicated, sadness comes from experience…” #podcast #sad #music #hiphop #latin | 8 | Show |
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| 360. | Sad Boy Radio LXIV: Know Yourself, Know Your Worth? (W/ Lee McIntosh of Lyrical Lemonade) | 8 | |
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| 361. | June 6, 2024 | 10 | |
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| 362. | Sad Boy Radio LXIX: Love Yourself First? (W/ Mamicana) | 8 | Show |
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| 363. | “We tend to rely on others instead of doing what got their attention in the first place” #podcast | 8 | Show |
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| 364. | Sad Boy Radio LXVI: Broken Promises? (W/ Mela-D) | 8 | |
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| 365. | Sad Boy Radio XCI: Can't Control Everything? (W/ M-Dok of Los DSVLDS) | 8 | Show |
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| 366. | Sad Boy Radio XC: The Things I Can't Change? (W/ Valcarcel of PVTSTCK) | 8 | |
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| 367. | You gotta be accountable for the things you do to make yourself suffer #podcast #mentalhealth #music | 8 | Show |
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| 368. | Sad Boy Radio XX:The Struggle is Real? | 8 | |
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| 369. | “I’m just A PART of the program” #podcast #mentalhealth #music | 67 | Show |
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| 370. | “I had to break certain relationships to chase my dream” #podcast #music #mentalhealth | 17 | Show |
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| 371. | “Sometimes the things you want are just not meant for you to have” #podcast #mentalhealth #music | 8 | Show |
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| 372. | Sad Boy Radio XXXIV: New Year New Problems? (W/ Adrian Almaraz) | 8 | Show |
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| 373. | Sad Boy Radio XXXIX: In Due Time? (W/ Mia Alva) | 8 | Show |
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| 374. | “Happiness is something gotta fight for each & every single day” #podcast #music #mentalhealth #rnb | 8 | Show |
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| 375. | “Females & MALES have daddy issues" #podcast #mentalhealth #music | 8 | Show |
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| 376. | “Sometimes we want things to work so bad, but don’t realize that it’s not meant for us” #podcast | 7 | Show |
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| 377. | “You grow around your traumas while they stay the same size” #music #mentalhealth #podcast | 7 | Show |
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| 378. | “I’ve struggled being my 100% self my whole life” #podcast #mentalhealth #music | 9 | |
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| 379. | Sad Boy Radio CI: Who's Really Got Me? (W/ Gato The DJ) | 7 | Show |
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| 380. | Sad Boy Radio CXXVII: Life's A Blessin? (Lil Blessin Interview) | 7 | |
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| 381. | “Something you love is ALWAYS gonna pull on something you want" #podcast #mentalhealth #music | 8 | |
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| 382. | “What is it we’re chasing when all our accomplishments mean nothing? | 7 | |
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| 383. | Sad Boy Radio XCV: Change For The Better? | 7 | Show |
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| 384. | Sad Boy Radio XCIII: Para La Cultura? (W/ LITE ) | 7 | Show |
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| 385. | “How can i be okay if I’m still grieving who I was yesterday?” #podcast #mentalhealth #music #dance | 7 | Show | Changes
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| 386. | HotRod Interview: Talks JOINING WGCI, Losing His Father, Chicago Community & MORE | Sad Boy Radio | 12 | Show |
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| 387. | “Nobody wants to admit that they don’t love themselves” #podcast #music #mentalhealth | 8 | Show |
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| 388. | Sad Boy Radio XIV: Risk it All? (W/ Steven Walsh) | 7 | |
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| 389. | Sad Boy Radio X: Why so Negative? | 7 | |
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| 390. | Sad Boy Radio CVIII: What's The World Without Enigma? (W/ DJ Enigma The Villain) | 6 | Show |
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| 391. | Sad Boy Radio CIV: Healing My Scars? (W/ Yaya Tha Bawse) | 6 | |
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| 392. | Sad Boy Radio LIII: Memories Past Lover's Lane? (W/ Josh K) | 6 | |
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| 393. | “Im putting on a fake smile, but dealing with so much BS behind the scenes” #mentalhealth #podcast | 6 | Show |
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| 394. | "What’re you doing to remain successful” #podcast #mentalhealth #music | 6 | Show |
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| 395. | “How do you express your love for music when you don’t make it?” #podcast #mentalhealth #music | 8 | |
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| 396. | “I can’t celebrate my wins because I was always told I could do better growing up” #podcast #music | 6 | Show |
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| 397. | Sad Boy Radio CXVI: Outta Time? (Rick Dawg Interview) | 6 | |
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| 398. | Sad Boy Radio LVI: Looking For Myself? ( W/ Jax of V5) | 6 | Show |
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| 399. | “We search for a new safety when we lose our person” #podcast #mentalhealth #music | 7 | |
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| 400. | Sad Boy Radio VI: What is the Purpose of Life? | 6 | |
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