| 1. | Pierre "Peeweedaplug" Andresen on LEAVING House of Highlights, ESPN, Music & MORE | Sad Boy Radio | 36 | |
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| 2. | "I LOST hope when King Von died” #mentalhealth #podcast #music | 35 | Show |
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| 3. | Sad Boy Radio LXXVIII: Lose You To Love Me? (W/ Mercocet) | 23 | |
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| 4. | “Trauma will make you forget things very quickly” #podcast #mentalhealth #music | 22 | Show |
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| 5. | “I don’t even trust Uber drivers" #podcast #mentalhealth #music | 19 | |
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| 6. | Sad Boy Radio CIII: Where I'm From? (W/ OG Denzo) | 16 | Show |
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| 7. | “The younger generation just needs guidance” #podcast #mentalhealth #music | 14 | Show |
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| 8. | “There’s street dudes who live this life because they’re forced to” #podcast #mentalhealth #music | 14 | |
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| 9. | “Forgiveness can’t come with resentment” #podcast #mentalhealth #music | 12 | |
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| 10. | “Your youth ends when you experience loss for the first time” #podcast #mentalhealth #music | 12 | Show |
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| 11. | "God’s timing is always right” #podcast #mentalhealth #music | 12 | Show |
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| 12. | Sad Boy Radio LXXXII: I'm Solo? (W/ SoloCelo) | 11 | Show |
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| 13. | “I only knew the ‘WRONG’ crowd growing up” #podcast #mentalhealth #music | 11 | |
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| 14. | Sad Boy Radio XXXIV: New Year New Problems? (W/ Adrian Almaraz) | 10 | Show |
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| 15. | Sad Boy Radio XXXVIII: Me, Myself, & I? (W/ Soski) | 10 | Show |
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| 16. | “Nothing felt real about losing my family” #podcast #music #mentalhealth | 9 | Show |
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| 17. | “People with depression want to function, they just physically can’t” #podcast #mentalhealth #music | 9 | Show |
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| 18. | “If you’re not reciprocating my effort it’s just not meant to be” #podcast #mentalhealth #music | 8 | |
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| 19. | Sad Boy Radio LXXV: The Way You Shaped Me? ( W/ Ozzy Arias) | 8 | |
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| 20. | Eddy Mack Interview: Talks QUITTING music, Battling Depression, & Palestine | Sad Boy Radio | 8 | |
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| 21. | Sad Boy Radio CXXV: Better Than I Was? (Flex Sinatra Interview) | 8 | |
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| 22. | “Lebron dunked on me & I got BENCHED for 20 games” #podcast #mentalhealth #nba | 8 | Show |
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| 23. | “All ya’ll ain’t gonna live” #podcast #mentalhealth #music | 8 | Show |
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| 24. | “Sometimes i don’t have the words to articulate how i feel” #podcast #mentalhealth #music | 8 | |
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| 25. | Chianthony Lee Interview: Battling Depression, LiveNation, Entrepreneurship + MORE | Sad Boy Radio | 7 | |
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| 26. | Sad Boy Radio LVIII: Am I Good Enough? (W/ Stevensjpeg) | 7 | |
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| 27. | “I’m TRAUMATIZED from building failed relationships” #podcast #mentalhealth #music | 7 | Show |
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| 28. | Sad Boy Radio XXVIII: Bad Endings & Fresh Starts? (W/ Mia Alva) | 7 | Show |
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| 29. | Sad Boy Radio CXXXVI: Real Life? (Workrate Interview) | 7 | |
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| 30. | “When something bad happens people show up out of nowhere & leave just as quick” #healing #podcast | 7 | Show |
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| 31. | Fastmoney Ant Interview: Mental Health, Legal Trouble, Growing Up In Chicago + MORE | Sad Boy Radio | 7 | | Growing Up
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| 32. | “If people don’t align with my vision, they gotta go” #podcast #mentalhealth #music | 7 | Show |
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| 33. | “I only care about what I care about” #podcast #mentalhealth #music | 7 | Show |
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| 34. | “I keep asking you to fix certain things, hoping it’ll change” #podcast #mentalhealth #music | 6 | Show |
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| 35. | “It’s very refreshing to start new with someone else” #podcast #music #mentalhealth | 6 | Show |
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| 36. | “You can’t expect someone to make you happy if you can’t make yourself happy” #podcast #mentalhealth | 6 | Show |
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| 37. | “You’re mourning someone who’s still alive, because they’re no good for you” #podcast #mentalhealth | 6 | Show |
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| 38. | “You’re in the wrong friend group if you’re the smartest one” #podcast #mentalhealth #music | 6 | Show |
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| 39. | It feels like you’re in a place of no return when nothing in the world can fix your situation… #rap | 6 | |
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| 40. | Sad Boy Radio LXXIX: Focusing on Me? (W/ Zae Visuals) | 6 | |
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| 41. | “I don’t want to think your burdens are mine to carry” #podcast #music #mentalhealth | 6 | Show |
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| 42. | “You are not defined by your past” #podcast #mentalhealth #music | 6 | Show |
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| 43. | “SOMETHING is affecting you, and you don’t have the answers to solve it” #podcast #mentalhealth | 6 | |
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| 44. | “Love is unconditional, no matter what has happened” #podcast #love #music | 6 | Show |
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| 45. | “God got his purpose for everyone” #podcast #mentalhealth #music | 6 | Show |
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| 46. | Sad Boy Radio CII: Proving My Worth? ( W/ Gualo Hawes) | 5 | Show |
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| 47. | Sad Boy Radio CXXXVII: Never Settle? (Hypno Carlito Interview) | 5 | |
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| 48. | “I can’t accept love the way I would like to give it” #podcast #mentalhealth #music | 5 | Show |
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| 49. | “I wanted to be loved so bad, I was accepting it from anyone.” #podcast #mentalhealth #music | 5 | |
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| 50. | Sad Boy Radio LXXXVII: Never Thought I'd Be Here? ( W/ Sketchy Frankie) | 5 | Show |
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| 51. | Sad Boy Radio XI: Letter to My Grandmas? (Cherish Those Around You) | 5 | |
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| 52. | Sergio Esparza Interview: Talks Sexxy Redd, No More Heroes, QUITTING School & MORE | Sad Boy Radio | 5 | Show | No More Heroes
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| 53. | “I’ve been hurt so much, it’s hard for me to let people in” #podcast #mentalhealth #music | 5 | Show |
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| 54. | “Why do I feel bad if I’ve forgiven the action?” #podcast #mentalhealth #music | 5 | |
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| 55. | “IM NOT STATISTIC” #podcast #mentalhealth #music | 5 | Show |
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| 56. | “I not ready for a relationship” #podcast #mentalhealth #music | 5 | |
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| 57. | Sad Boy Radio C: I'm Only Human? (W/ DJ SIMMY) | 5 | Show |
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| 58. | “If you stay where you’re not supposed to be, you look crazy” #podcast #mentalhealth #music | 4 | |
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| 59. | DJ DRIP INTERVIEW: Talks HITTING Rock Bottom, V5, Súbelo Sunday & MORE | Sad Boy Radio | 4 | |
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| 60. | Sad Boy Radio CXX: Outgrowing The Old Me? (Bae Wicked Interview) | 4 | |
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| 61. | “You never wanna drink because you’re feeling a negative emotion” #podcast #music #mentalhealth | 4 | Show |
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| 62. | “We’ve all been the person that somebody should’ve let go of” #podcast #relationship #music | 4 | Show |
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| 63. | Sad Boy Radio CXXI: My Past Doesn't Define Me? (Daylight Tone Interview) | 4 | |
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| 64. | “Happiness is the end of growth” #podcast #mentalhealth #music | 4 | |
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| 65. | “Why would I ever want to conform to a room” #podcast #mentalhealth #music | 4 | Show |
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| 66. | Sad Boy Radio XLVIII: Fake People Showing Fake Love to Me? ( W/ Rodeo of The Future Kingz) | 4 | Show |
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| 67. | “I wanna do whatever I can to live my best life” #drake #dj #podcast #advice #rnb #hiphop #latino | 4 | Show |
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| 68. | Sad Boy Radio LXXXVIII: Where's The Stability? (W/ DAM DAM of Pivot Gang) | 4 | Show |
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| 69. | “Your first car is where a lot of growing up happens” #podcast #femdot #chicago #music #hiphop | 4 | Show |
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| 70. | Sad Boy Radio: Soy El Mismo? ( W/ J Santos of Los DSVLDS) | 4 | Show |
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| 71. | Recoechi Interview: Sway in The Morning, HEALING From Trauma, Community + MORE | Sad Boy Radio | 4 | |
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| 72. | “People look at you different when they know you have an education” #podcast #mentalhealth #music | 4 | Show |
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| 73. | Sad Boy Radio XV: What Makes You... You? | 4 | |
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| 74. | Sad Boy Radio CXXVII: Life's A Blessin? (Lil Blessin Interview) | 4 | |
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| 75. | “There’s moments of joy even in the saddest parts of our life” #podcast #music #mentalhealth | 4 | Show |
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| 76. | “Do I have hope that I can be happy tomorrow?” #podcast #mentalhealth #music | 4 | Show |
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| 77. | “You come up with various reasons to stay in a toxic relationship” #podcast #mentalhealth #music | 4 | Show |
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| 78. | “I feel like nobody was seeing what I was going through” #podcast #music #mentalhealth | 4 | Show |
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| 79. | “My grandma made sure I did everything I wanted to do” #podcast #mentalhealth #music | 4 | Show |
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| 80. | Sad Boy Radio XLII: You Are Not The Father? (W/ DJ Drip) | 4 | |
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| 81. | “I can’t allow my love for someone to blind me & tear me down” #drake #podcast #friends #latino #rnb | 4 | Show |
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| 82. | Sad Boy Radio XXXII: Something is Always Missing? | 4 | |
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| 83. | BigKayBeezy Interview: Dropped MURDER Charge, LEAVING Street Life, Polo G & MORE | Sad Boy Radio | 3 | |
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| 84. | “Watching people on social media makes you feel like you’re behind” #podcast #mentalhealth #music | 3 | Show |
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| 85. | “I want to know what happiness looks like outside of business as well” #podcast #music #mentalhealth | 3 | Show |
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| 86. | “It’s not fair for beauty standards to hold women back in the industry” #podcast #women #music #rnb | 3 | Show |
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| 87. | “Why would you hurt me after I told you about my wounds?” #podcast #music #mentalhealth | 3 | Show |
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| 88. | “History doesn’t necessarily repeat itself, but it rhymes” #podcast #mentalhealth #music | 3 | Show |
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| 89. | “I’ve outgrown being under appreciated” #podcast #mentalhealth #music | 3 | Show |
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| 90. | Everyday you should figure out how to be a better you than yesterday #podcast #music #mentalhealth | 3 | Show |
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| 91. | “People will hate you for the sole fact everyone else supports you” #podcast #rapper #sadboyradio | 3 | Show |
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| 92. | “What do you do when you’re so anxious you shut down?” #podcast #mentalhealth #music | 3 | Show |
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| 93. | “Am I gonna look back & regret not hanging out with my friends?” #podcast #mentalhealth #music | 3 | Show |
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| 94. | “I didn’t have a purpose in life” #purpose #usher #justinbieber #lost #hiphop #podcast | 3 | |
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| 95. | “Anything I ever said or DID, I did in my own” #podcast #mentalhealth #music | 3 | |
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| 96. | Sad Boy Radio LXXXV: Finding My Balance? ( W/ First Class Bee) | 3 | |
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| 97. | Sad Boy Radio XCVIII: Hoping To Be Okay? (W/ Danielle Casel of No More Heroes) | 3 | Show | No More Heroes
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| 98. | “I’m traumatized by my old relationships” #podcast #mentalhealth #music | 3 | |
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| 99. | “How do you pull somebody out of a hole they don’t wanna come out of” #podcast #music #mentalhealth | 3 | Show |
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| 100. | “I don’t like picking up other people’s issues” #podcast #music #mentalhealth #drake | 3 | Show |
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