| 2023-02-15 | “Everybody has to think that I got something going on…” #drake #mentalhealth #podcast #chicago | 0:31 | 1,004 | Show |
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| 2023-02-14 | “I can only know you to the deepest level you know yourself” #chrisbrown #love #podcast #music #rnb | 0:31 | 447 | Show |
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| 2023-02-13 | “I was burnt out after we failed” #saba #smoko #chicago #pvtstck #podcast #music #mentalhealth #rnb | 0:49 | 1,325 | Show |
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| 2023-02-12 | “My trauma response allowed me to create PVTSTCK” #justinbieber #trauma #podcast #pvtstck #chicago | 0:29 | 1,610 | Show |
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| 2023-02-12 | “My depression stems from wanting my mom’s validation” #mama #augustalsina #podcast #mentalhealth | 0:40 | 1,183 | Show |
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| 2023-02-11 | “I created a persona i didn’t know how to be anymore” #podcast #drake #music #mentalhealth #chicago | 0:36 | 1,058 | Show |
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| 2023-02-10 | Sad Boy Radio XC: The Things I Can't Change? (W/ Valcarcel of PVTSTCK) | 41:52 | 190 | |
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| 2023-02-10 | “People are gonna talk whether you’re winning or losing” #podcast #rapper #interview #music #hiphop | 0:31 | 851 | Show |
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| 2023-02-08 | “My pops told me the more people you’re with the more you got to watch yourself” #podcast #music | 0:27 | 2,628 | Show |
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| 2023-02-07 | “People will hate you for the sole fact everyone else supports you” #podcast #rapper #sadboyradio | 0:36 | 2,336 | Show |
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| 2023-02-03 | Sad Boy Radio LXXXIX: Can't Grow With Everyone? (W/ OG Stevo) | 48:55 | 253 | Show |
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| 2023-01-28 | Sad Boy Radio LXXXVIII: Where's The Stability? (W/ DAM DAM of Pivot Gang) | 1:00:02 | 188 | Show |
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| 2023-01-23 | “What is it we’re chasing when all our accomplishments mean nothing? | 0:53 | 329 | |
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| 2023-01-20 | Sad Boy Radio LXXXVII: Never Thought I'd Be Here? ( W/ Sketchy Frankie) | 36:40 | 198 | Show |
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| 2023-01-18 | “Every man lives two lives, and his second one starts when he realizes you only live once” | 0:45 | 360 | |
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| 2023-01-06 | Sad Boy Radio LXXXV: Finding My Balance? ( W/ First Class Bee) | 56:44 | 487 | |
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| 2022-12-31 | Sad Boy Radio LXXXIV: It Get's Worse Before It Gets Better? ( W/ Big Vic) | 38:02 | 65 | Show |
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| 2022-12-23 | Sad Boy Radio LXXXIII: Back To Square One? (W/ Kid Nimbus) | 49:07 | 265 | Show |
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| 2022-12-16 | Sad Boy Radio LXXXII: I'm Solo? (W/ SoloCelo) | 56:58 | 653 | Show |
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| 2022-12-10 | Sad Boy Radio LXXXI: The Moments We Miss? (W/ Gold Haze) | 51:42 | 103 | Show |
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| 2022-12-02 | Sad Boy Radio LXXX: What's Really Holding Me Back? (W/ ESCHICANO) | 59:28 | 230 | |
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| 2022-11-26 | Sad Boy Radio LXXIX: Focusing on Me? (W/ Zae Visuals) | 39:26 | 382 | |
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| 2022-11-18 | Sad Boy Radio LXXVIII: Lose You To Love Me? (W/ Mercocet) | 47:36 | 967 | |
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| 2022-11-11 | Sad Boy Radio LXXVII: Where Did The Time Go? (W/ Marce) | 52:14 | 294 | |
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| 2022-11-04 | Sad Boy Radio LXXVI: For This Life I Cannot Change? (W/ Dre Wicked) | 45:31 | 284 | |
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| 2022-10-28 | Sad Boy Radio LXXV: The Way You Shaped Me? ( W/ Ozzy Arias) | 45:23 | 478 | |
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| 2022-10-21 | Sad Boy Radio LXXIV: Where Is The Love? ( W/ Chapulin) | 34:10 | 461 | |
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| 2022-10-16 | Sad Boy Radio LXXIII: What Would My Life Have Been? ( W/ DJ O-ZONE) | 1:26:09 | 441 | |
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| 2022-10-07 | Sad Boy Radio LXXII: Searching for Peace? (W/ DJ Payday) | 39:38 | 227 | Show |
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| 2022-09-30 | Sad Boy Radio LXXI: Ask Myself Questions You Have, But You Won't Ask? (W/ Bodhi) | 46:35 | 109 | Show |
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| 2022-09-25 | Sad Boy Radio LXX: Love You From Afar? ( W/ Demir of Published Studios) | 49:36 | 157 | |
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| 2022-09-16 | Sad Boy Radio LXIX: Love Yourself First? (W/ Mamicana) | 47:34 | 151 | Show |
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| 2022-09-09 | Sad Boy Radio LXVIII: It'll Be Okay Someday? (W/ GloUp Jake of Lyrical Lemonade) | 58:51 | 283 | Show |
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| 2022-09-02 | Sad Boy Radio LXVII: Nothing Was The Same? ( W/ Kique) | 48:25 | 249 | Show |
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| 2022-08-26 | Sad Boy Radio LXVI: Broken Promises? (W/ Mela-D) | 51:41 | 282 | |
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| 2022-08-19 | Sad Boy Radio LXV: How Do I Go On? ( W/ FILM of V5 & Vision55) | 38:20 | 273 | |
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| 2022-08-12 | Sad Boy Radio LXIV: Know Yourself, Know Your Worth? (W/ Lee McIntosh of Lyrical Lemonade) | 45:57 | 130 | |
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| 2022-08-06 | Sad Boy Radio XLIII: I'm ENTLD To Be Happy? (W/ AK of ENTLD) | 1:20:29 | 252 | Show |
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| 2022-07-29 | Sad Boy Radio LXII: Mi Error Favorito ( W/ JBro Bugatti) | 35:05 | 231 | |
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| 2022-07-22 | Sad Boy Radio LXI: Bop King of Chicago? (W/ DLOW) | 59:16 | 190 | | The King of Chicago
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| 2022-07-15 | Sad Boy Radio LX: Why Did I Meet You? ( W/ Preme) | 53:32 | 140 | |
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| 2022-07-08 | Sad Boy Radio LIX: I'm Not Ready For Love? ( W/ Kique) | 45:15 | 292 | Show |
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| 2022-07-01 | Sad Boy Radio LVIII: Am I Good Enough? (W/ Stevensjpeg) | 44:00 | 200 | |
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| 2022-06-24 | Sad Boy Radio LVII: All Hail The King? (W/ King Inesse) | 51:25 | 1,240 | Show |
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| 2022-06-17 | Sad Boy Radio LVI: Looking For Myself? ( W/ Jax of V5) | 46:03 | 316 | Show |
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| 2022-06-10 | Sad Boy Radio LV: I'm Hurting, But What's Art Without Pain? (W/ Baka of KNVS) | 49:49 | 213 | |
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| 2022-06-03 | Sad Boy Radio LIV: "You Ain't F***k With Me Then But How Bout Now?" (W/ Equan) | 57:42 | 220 | |
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| 2022-05-27 | Sad Boy Radio LIII: Memories Past Lover's Lane? (W/ Josh K) | 51:54 | 83 | |
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| 2022-05-20 | Sad Boy Radio: It's The Simple Things In Life We Forget? (W/ Sydny August of OTF) | 34:56 | 84 | |
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| 2022-05-13 | Sad Boy Radio: Am I The The Broken One? (W/ BeatsByLexx) | 41:28 | 328 | |
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| 2022-05-06 | Sad Boy Radio: Soy El Mismo? ( W/ J Santos of Los DSVLDS) | 42:10 | 542 | Show |
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| 2022-04-29 | Sad Boy Radio XLIX: Somebody That I Used To Know? (W/ Hayward of KNVS) | 48:03 | 145 | Show |
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| 2022-04-24 | Sad Boy Radio XLVIII: Fake People Showing Fake Love to Me? ( W/ Rodeo of The Future Kingz) | 39:53 | 133 | Show |
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| 2022-04-15 | Sad Boy Radio XLVII: I'm Kewl Being Alone? (W/ Kewl) | 54:45 | 466 | Show |
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| 2022-04-08 | Sad Boy Radio XLVI: When I See You Again? (W/ Isa) | 56:04 | 206 | Show |
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| 2022-04-01 | Sad Boy Radio XLV: Never Satisfied With Life? (W/ Nico Supremo) | 1:09:49 | 132 | |
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| 2022-03-29 | Sad Boy Radio: ONE YEAR? (W/ SBR MVT) | 14:43 | 69 | Show |
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| 2022-03-25 | Sad Boy Radio XLIII: "She Changed My Life?" (Fatherhood) [W/ Narkalix] | 49:39 | 107 | |
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| 2022-03-19 | Sad Boy Radio XLII: You Are Not The Father? (W/ DJ Drip) | 1:06:08 | 1,052 | |
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| 2022-03-12 | Sad Boy Radio XLI: Loyal to a Fault? (Lost episode) | 2:23 | 139 | Show |
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| 2022-03-04 | Sad Boy Radio XL: What Is Happiness? (W/ Ceasedays) | 1:18:07 | 245 | Show |
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| 2022-02-26 | Sad Boy Radio XXXIX: In Due Time? (W/ Mia Alva) | 35:37 | 213 | Show |
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| 2022-02-18 | Sad Boy Radio XXXVIII: Me, Myself, & I? (W/ Soski) | 41:01 | 636 | Show |
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| 2022-02-11 | Sad Boy Radio XXXVII: Can I Count On You? (Dropping Gems) [W/ TFK Co-Founder Allen The Official] | 59:01 | 106 | |
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| 2022-02-05 | Sad Boy Radio XXXVI: Finding Myself & You'll Be Waiting Forever? (W/ Drew The Kiiid) | 45:16 | 110 | |
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| 2022-01-28 | Sad Boy Radio XXXV: What Does Music Mean to You? (W/ Exjames12) | 29:33 | 84 | |
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| 2022-01-21 | Sad Boy Radio XXXIV: New Year New Problems? (W/ Adrian Almaraz) | 32:34 | 124 | Show |
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| 2021-12-31 | SBR XXXIII: Let's Close This Chapter? (EOY) | 42:24 | 71 | |
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| 2021-12-25 | Sad Boy Radio XXXII: Something is Always Missing? | 42:43 | 104 | |
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| 2021-12-17 | Sad Boy Radio XXXI: Bad Habits? (W/ PIWA) | 38:37 | 61 | |
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| 2021-12-03 | Sad Boy Radio XXX: Did it Even Matter? (W/ Protein Papi) | 39:52 | 160 | |
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| 2021-11-19 | Sad Boy Radio XXIX: Life Moves Fast & It Stops For No One? (W/ Johnny Carter) | 35:38 | 72 | Show |
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| 2021-11-12 | Sad Boy Radio XXVIII: Bad Endings & Fresh Starts? (W/ Mia Alva) | 31:39 | 343 | Show |
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| 2021-10-30 | Sad Boy Radio XXVII: Follow Your Dreams? | 41:43 | 94 | |
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| 2021-10-15 | Sad Boy Radio XXVI: Life Ain't Easy in your Twenties? (W/ Adam Martinez) | 37:47 | 87 | Show |
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| 2021-10-08 | Sad Boy Radio XXV: Love is Complicated? | 41:14 | 105 | Show |
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| 2021-09-26 | Sad Boy Radio XXIV: What Did you Expect? | 40:00 | 60 | |
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| 2021-09-17 | Sad Boy Radio XXIII: Are you the One? | 46:18 | 122 | |
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| 2021-09-03 | Sad Boy Radio XXII: Forever Changing? | 22:50 | 79 | |
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| 2021-08-29 | Sad Boy Radio XXI: Thank you? | 3:03 | 133 | |
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| 2021-08-21 | Sad Boy Radio XX:The Struggle is Real? | 43:32 | 63 | |
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| 2021-08-13 | Sad Boy Radio XIX: Too Late? | 30:44 | 94 | |
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| 2021-07-30 | Sad Boy Radio XVIII: Live in the Moment? | 28:01 | 49 | |
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| 2021-07-23 | Sad Boy Radio XVII: What Are Your Milestones? (W/ Tora Woloshin) | 25:21 | 70 | |
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| 2021-07-17 | Sad Boy Radio XVI: What inspires You? | 31:37 | 53 | |
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| 2021-07-09 | Sad Boy Radio XV: What Makes You... You? | 29:55 | 155 | |
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| 2021-07-02 | Sad Boy Radio XIV: Risk it All? (W/ Steven Walsh) | 33:51 | 73 | |
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| 2021-06-25 | Sad Boy Radio XIII: Money is Evil? | 20:35 | 41 | |
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| 2021-06-18 | Sad Boy Radio XII: Next Steps in Life? | 30:14 | 90 | |
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| 2021-06-11 | Sad Boy Radio XI: Letter to My Grandmas? (Cherish Those Around You) | 6:16 | 58 | |
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| 2021-06-04 | Sad Boy Radio X: Why so Negative? | 27:47 | 64 | |
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| 2021-05-28 | Sad Boy Radio IX: True to Self? | 29:05 | 198 | |
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| 2021-05-21 | Sad Boy Radio VIII: Remember Me? | 27:41 | 130 | |
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| 2021-05-14 | Sad Boy Radio VII: The Drugs Are Talking & No One is Listening? | 34:06 | 81 | |
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| 2021-05-07 | Sad Boy Radio VI: What is the Purpose of Life? | 31:01 | 82 | |
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| 2021-04-30 | Sad Boy Radio V: Does Time Heal All Wounds? | 32:20 | 127 | |
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| 2021-04-23 | Sad Boy Radio IV: Toxic Relationships? | 30:05 | 123 | |
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| 2021-04-16 | Sad Boy Radio III: Who Am I? | 28:17 | 75 | |
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| 2021-04-09 | Sad Boy Radio II: What Made You This Way? | 28:33 | 114 | |
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| 2021-03-30 | Sad Boy Radio: What Would Fame Do to You? | 27:19 | 198 | |
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