| 401. | Sad Boy Radio XLI: Loyal to a Fault? (Lost episode) | 6 | Show |
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| 402. | “We search for a new safety when we lose our person” #podcast #mentalhealth #music | 7 | |
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| 403. | Sad Boy Radio LXII: Mi Error Favorito ( W/ JBro Bugatti) | 6 | |
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| 404. | Sad Boy Radio CXXIV: Trust Issues? (Kvdoe Interview) | 6 | Show |
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| 405. | Sad Boy Radio LIII: Memories Past Lover's Lane? (W/ Josh K) | 6 | |
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| 406. | “We only HAVE so much energy to give before letting go” #podcast #mentalhealth #music | 6 | |
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| 407. | “Certain people aren’t for you” #podcast #mentalhealth #music | 8 | Show |
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| 408. | “Leaving certain relationships is necessary for YOUR own growth" #podcast #mentalhealth #music | 9 | Show |
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| 409. | Sad Boy Radio XXVII: Follow Your Dreams? | 6 | |
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| 410. | Sad Boy Radio CIV: Healing My Scars? (W/ Yaya Tha Bawse) | 6 | |
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| 411. | Sad Boy Radio CVIII: What's The World Without Enigma? (W/ DJ Enigma The Villain) | 6 | Show |
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| 412. | Sad Boy Radio CXVI: Outta Time? (Rick Dawg Interview) | 6 | |
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| 413. | “Would I be happy having everything I wanted, but all alone” #podcast #mentalhealth #music | 7 | Show |
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| 414. | Sad Boy Radio LIV: "You Ain't F***k With Me Then But How Bout Now?" (W/ Equan) | 5 | |
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| 415. | “I would internalize others issues & think there was something wrong with me…” #podcast #advice #rnb | 5 | Show |
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| 416. | “As soon as you find that thing that gives you peace, it’s the best feeling in the world” #podcast | 5 | Show |
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| 417. | Sad Boy Radio XV: What Makes You... You? | 5 | |
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| 418. | Sad Boy Radio XCI: Why I Run Away? (W/ Ausar) | 5 | |
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| 419. | “Everybody has a reason for why they’ve become the person you see” #podcast #frankocean #chicago | 5 | Show |
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| 420. | “Everybody has to think that I got something going on…” #drake #mentalhealth #podcast #chicago | 5 | Show |
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| 421. | Sad Boy Radio XXXI: Bad Habits? (W/ PIWA) | 5 | |
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| 422. | “You have to love yourself before anything good happens in life” #podcast #mentalhealth #music | 5 | Show |
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| 423. | SBR XXXIII: Let's Close This Chapter? (EOY) | 5 | |
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| 424. | “Sometimes everything has to fall apart for it to get better” #podcast #mentalhealth #music | 6 | Show |
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| 425. | Sad Boy Radio XIX: Too Late? | 5 | |
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| 426. | “You got two weeks & then they’re gonna forget you” #podcast #mentalhealth #music | 27 | Show |
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| 427. | Sad Boy Radio XII: Next Steps in Life? | 5 | |
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| 428. | Sad Boy Radio XXXVI: Finding Myself & You'll Be Waiting Forever? (W/ Drew The Kiiid) | 5 | |
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| 429. | Sad Boy Radio CXVII: Trynna Heal? (SONNY Interview) | 5 | |
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| 430. | Sad Boy Radio LXXX: What's Really Holding Me Back? (W/ ESCHICANO) | 5 | |
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| 431. | “I didn’t think anything could be taken away from me…” #podcast #mentalhealth #usher #music #latino | 5 | Show |
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| 432. | "Not everybody’s dreams MAKE sense, and that’s okay” #podcast #mentalhealth #music | 5 | Show |
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| 433. | Sad Boy Radio CXV: Pivot My Life? (FRSH WATERS of Pivot Gang Interview) | 5 | |
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| 434. | Richaun Holmes Interview: Journey to NBA, Wizards Trade, IMPORTANCE of Family & MORE | Sad Boy Radio | 11 | Show |
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| 435. | “Music helps me connect to people & share emotions” #podcast #mentalhealth #music | 5 | Show |
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| 436. | Sad Boy Radio LXXI: Ask Myself Questions You Have, But You Won't Ask? (W/ Bodhi) | 5 | Show |
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| 437. | Sad Boy Radio CXXXIIII: Learning To Forgive? (D2X Interview) | 7 | |
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| 438. | “I started to fear failure once everyone was watching” #podcast #mentalhealth #nba | 55 | Show |
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| 439. | Sad Boy Radio XXII: Forever Changing? | 5 | |
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| 440. | “Women in the entertainment industry are the most vulnerable” #music #girls #dj #music #podcast #rnb | 5 | Show |
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| 441. | “God got a specific path for you” #mentalhealth #music #podcast | 5 | Show |
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| 442. | “You start trying to fill everybody’s cup & eventually you’re pouring from an empty cup” #podcast | 5 | Show |
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| 443. | Sad Boy Radio CVII: The Things I'll Never Have? (W/ TRUB) | 5 | |
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| 444. | “Because this isn’t toxic I don’t think this person is interested” #podcast #mentalhealth #music | 12 | |
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| 445. | “People can fall in love with who you were just by the stories you told…” #podcast #mentalhealth | 5 | Show |
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| 446. | “Check on your people even if they seem okay” #podcast #mentalhealth #music | 5 | |
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| 447. | “Am I gonna push myself so hard in my career that I don’t have a family later?” #podcast #music #rnb | 4 | Show |
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| 448. | “I’m basically saying to all my old situations ‘it was fun while it lasted’” #podcast #mentalhealth | 4 | Show |
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| 449. | Sad Boy Radio CXXIII: What Is Your Reason? (Chris Classick Interview) | 4 | |
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| 450. | “I felt defeated having to go back & tell everyone we’re not getting signed…” #podcast #music #rnb | 4 | Show |
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| 451. | “Would you be happy having to sacrifice memories for success” #podcast #mentalhealth #music | 4 | |
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| 452. | “When you’re at your lowest you wonder if it’s even worth it” #mentalhealth #podcast #theweeknd #rnb | 4 | Show |
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| 453. | “We ain’t made it yet but there’s people who wish they were in our positions” #podcast #hiphop #rap | 4 | Show |
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| 454. | “Being told you’re not good enough will stick with you” #podcast #mentalhealth #music | 7 | |
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| 455. | Sad Boy Radio XXIII: Are you the One? | 4 | |
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| 456. | Sad Boy Radio CXXVI: Learning To Let Go? (KAMI Interview) | 6 | Show |
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| 457. | Sad Boy Radio XXIV: What Did you Expect? | 4 | |
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| 458. | Sad Boy Radio CXIX: Who I Could’ve Been? (KingTrey Interview) | 4 | |
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| 459. | “Music has this way of helping us express what can’t be said” #bigsean #podcast #music #chicago | 4 | Show |
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| 460. | “As a child you root for the hero, but as you get older you understand the villain” #podcast #music | 4 | Show |
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| 461. | Sad Boy Radio CXVIII: Everything Has Changed? (Mfn Melo Interview) | 4 | |
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| 462. | Fastmoney Ant Interview: Mental Health, Legal Trouble, Growing Up In Chicago + MORE | Sad Boy Radio | 12 | | Growing Up
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| 463. | Sad Boy Radio LXXXI: The Moments We Miss? (W/ Gold Haze) | 4 | Show |
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| 464. | SAD BOY RADIO ANNIVERSARY!! COP YOUR TICKETS! MARCH 31! #chicago #concert #jbrobugatti #reggaeton | 4 | |
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| 465. | “There has to be a deeper meaning to the things you do everyday” #podcast #chicago #latino #music | 4 | Show |
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| 466. | Sad Boy Radio XXXV: What Does Music Mean to You? (W/ Exjames12) | 4 | |
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| 467. | “I didn’t want to put on a disguise for a job” #podcast #job #goals #artist #music #chicago #latino | 4 | Show |
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| 468. | Sad Boy Radio XCIX: Everything Happens For A Reason? (W/ DJ PEEWEE) | 4 | |
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| 469. | Rich Robbins Interview: Soft & Tender, Societal Expectations, FORGIVENESS & MORE | Sad Boy Radio | 7 | |
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| 470. | Jaas Interview: HIATUS from Music, Infidelity, Toxic Relationships, Self-Love & MORE | Sad Boy Radio | 5 | |
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| 471. | “The fear set in when the expectations came in” #podcast #music #mentalhealth | 8 | Show |
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| 472. | Sad Boy Radio XXV: Love is Complicated? | 4 | Show |
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| 473. | Sad Boy Radio CXXXVII: Never Settle? (Hypno Carlito Interview) | 4 | |
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| 474. | “I need to know that at the end of this, you can’t say I’m just a rapper” #podcast #geazy #music | 4 | Show |
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| 475. | Sad Boy Radio CXXXV: 10 Years Later? (PVTSTCK INTERVIEW) | 9 | |
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| 476. | “At what point do you let go of who you once were?” #podcast#lloyd #growth #music #hiphop #latino | 4 | Show |
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| 477. | Sad Boy Radio XCVII: A N N I V E R S A R Y? (W/ Equan) | 4 | Show |
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| 478. | Sad Boy Radio XVI: What inspires You? | 3 | |
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| 479. | Sad Boy Radio LXXII: Searching for Peace? (W/ DJ Payday) | 3 | Show |
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| 480. | “You gotta take a loss to be great” #podcast #mentalhealth #music | 6 | Show |
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| 481. | “You are what you hang around” #podcast #mentalhealth #music | 6 | Show |
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| 482. | “Bad things will happen no matter what” | WORKRATE INTERVIEW #podcast #mentalhealth #music | 4 | Show |
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| 483. | I would always doubt myself, even after I accomplished something big #advice #podcast #justinbieber | 3 | Show |
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| 484. | “Everything I did, I did it because other people wanted me to” #mentalhealth #podcast #dj #miami | 3 | Show |
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| 485. | “I wasn’t taught to look at feelings as a priority growing up” #podcast #music #interview #femdot | 3 | Show |
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| 486. | “I was scared relationships would end if I said how I felt” #podcast #relationship #music #love | 3 | Show |
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| 487. | BigKayBeezy Interview: Dropped MURDER Charge, LEAVING Street Life, Polo G & MORE | Sad Boy Radio | 6 | |
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| 488. | Sad Boy Radio XXX: Did it Even Matter? (W/ Protein Papi) | 3 | |
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| 489. | “Everything made more sense once I went sober” #podcast #music #mentalhealth | 3 | Show |
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| 490. | Sad Boy Radio CXIV: Following My Path? (Remi Momson of No More Heroes Interview) | 3 | | No More Heroes
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| 491. | “I found my purpose through music after my mom passed” #podcast #music #mentalhealth | 3 | Show |
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| 492. | Sad Boy Radio CXXX: Never Switching Up? (Pronto Spazzout Interview) | 4 | Show |
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| 493. | Recoechi Interview: Sway in The Morning, HEALING From Trauma, Community + MORE | Sad Boy Radio | 8 | |
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| 494. | Sad Boy Radio LXI: Bop King of Chicago? (W/ DLOW) | 3 | | The King of Chicago
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| 495. | Sad Boy Radio XVIII: Live in the Moment? | 3 | |
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| 496. | “Pioneers never are the ones that benefit from leading the charge” #podcast #music #change #chicago | 3 | Show |
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| 497. | Gado 2X Interview: Talks Fatherhood, BREAKING Generational Curses, G Herbo & MORE | Sad Boy Radio | 7 | |
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| 498. | Sad Boy Radio XXVI: Life Ain't Easy in your Twenties? (W/ Adam Martinez) | 3 | Show |
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| 499. | Lotto Interview: Talks Lyrical Lemonade, Survivor's Guilt, Navigating Change + MORE | Sad Boy Radio | 9 | |
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| 500. | Sad Boy Radio XXIX: Life Moves Fast & It Stops For No One? (W/ Johnny Carter) | 3 | Show |
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