Worst Remakes; Best Sleepers, WTFs & More From 300 Episodes

Dave and Milt (the Chart Meister, not the Chart Master) celebrate what might be their 300th episode—give or take a few missed weeks and some lazy counting—by ditching the usual Billboard time-travel format and revisiting excerpts from their very first Past Tens episode from June 2019. They roast their early scripted, nervous energy, debate why certain catchphrases and categories stuck (Bad Remake, What the Fuck Were We Thinking, Never Heard Of It), and reminisce about recording in a Boston studio before switching to Zoom during COVID. Along the way they revisit early obsessions with Casey Kasem, grim “long distance dedication” letters, the terrifying TV movie Special Bulletin, awful and unnecessary covers, forgotten chart oddities, and beloved surprise discoveries like the Osmonds’ “Down by the Lazy River.” They close with a nostalgia debate, a fake monetization pitch, and promises of “300 more.”   Topics 02:00 Is This Episode 300?  02:52 Origin Story Enemy Lines 03:49 Anniversary Format Explained 06:02 Podcast Bits And Signposts 07:13 Replaying Episode One Intro 09:04 Early Nerves And No Scripts 12:42 Influences Hit Parade Rewatchables 15:16 Chartmeister Origins 17:46 Casey Kasem Dedication Clip 22:20 Pop Culture Flashback Special Bulletin 27:59 Bad Remakes Return 31:50 Guns N Roses Covers 32:59 Madonna Cover Disaster 33:44 Early Podcast Tech Chaos 35:55 Worst Hits Hall of Shame 40:53 Never Heard Of Gems 44:46 Osmonds Lazy River Surprise 46:48 Variety Show Flashback 51:24 Wild Trivia and Song Stories 56:17 Happy Days Nostalgia Theory 01:02:59 Anniversary Wrap and Goodbye