CoolKids Living Through Different Internets ( 4:54 - 6:21 ) CoolKids On Their Legacy & The World Shifting ( 16:09 - 18:27 ) CoolKids Speaks On The Time They Took A Break ( 22:13 - 24:11 ) Chuck On Sending Packs & AI For Sampling ( 24:19 - 27:43 ) CoolKids Share Their Experiences With Mac Miller ( 31:28 - 34:04 ) CoolKids Give Their MT Rushmore Of Blog Era ( 36:31 - 38:29 ) CoolKids Give Their Rap Album Of The Year ( 43:37 - 47:42 ) CoolKids Appreciating Alchemist's Work Ethic ( 48:32 - 50:11 ) * * * * * Sponsored by: ODDSOX - Best Sox for the Best Price https://www.oddsox.com use the promo code "BOOTLEGKEV" for 20% off at Check Out Sponsored by: Prize Picks - The Sports You Love All In One App https://prizepicks.onelink.me/ivHR/Bootleg get a "Play $5, Get $50 in Lineups" promotion by signing up for PrizePicks and using "BOOTLEG". Sponsored by: Jardín Las Vegas - Experience The Best Dispensary in Las Vegas https://www.jardinlasvegas.com @jardin_lasvegas Sponsored by: Rokin - America’s Leading Maker of Top-Quality Vape Pens. https://www.rokinvapes.com @rokinvapes Sponsored By: Pro Club - Comfort & Style since 1986 https://shopproclub.com @proclub_usa Bootleg Kev's 500th Episode Official Merch! T-Shirt Available here: https://www.bootlegkev.com/store-2