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