Ep 91 - Was Cyndi Bigger Than Madonna in The 80s? episode artwork

EPISODE · Apr 21, 2026 · 45 MIN

Ep 91 - Was Cyndi Bigger Than Madonna in The 80s?

from Tell Me Where I'm Going (Wrong) · host Josh Leuner and Sean O'Callaghan

In this latest episode of Tell Me Where I’m Going (Wrong), Josh and Sean discuss the cultural legacy of pop superstars Madonna and Cyndi Lauper, ahead of the release of Madonna’s new album Confessions on a Dance Floor II. They contemplate how, for a brief moment in 1983/early 1984, Cyndi was actually a bigger name than Madonna in mainstream culture even though Madonna obviously went on to eclipse Cyndi and most of her musical peers when it comes to longevity and fame.The pair then chat about the 10th anniversary of the death of musical legend Prince. They talk about where they were when they heard the news, the effect his death had on them, and attempt to list their favourite Prince songs which turns out to be an extremely tough task.This episode also touches on the current jet fuel crisis affecting the UK as a consequence of the US and Israel attacks on Iran and the ensuing blockade of the Straight of Hormuz. Coupled with new EU travel requirements including fingerprinting, European travel is seemingly on the verge of chaos.Enjoy the ride!#podcast #popculture #LGBTQ #CurrentAffairs #Iran #Madonna #Prince #CyndiLauper #USA #PetrolCrisisAbout the HostsJosh Leuner is a London-based singer and plant-geek. Find out more about him here:https://linktr.ee/joshandthejumpstarts Sean O’Callaghan is an award-winning blogger and published author. Find out more about him here:https://linktr.ee/fatgayvegan Theme MusicOur theme music is the song Empty Seat by Josh and The Jumpstarts   -  Stream it here: https://open.spotify.com/artist/4KxOAKJFWCoSWBMA99QEax?si=3Q_SjkQKTVuXANcrxmh95gOther things mentioned:Sean’s Prince playlist on Spotify:https://open.spotify.com/playlist/37sBCZCDTUylHTCyb6NeVm?si=295915fdb88d46b4Signup for London Vegan Beer Fest updates:https://www.veganbeerfest.co.ukChapters:00:00 Navigating Anxiety and Existential Thoughts03:03 Madonna's Musical Journey and Legacy05:54 The Impact of Ageism and Misogyny in Music08:51 Cyndi Lauper vs. Madonna: A Comparative Analysis11:56 The Evolution of Fame and Public Persona14:44 Cultural Impact and Legacy of Pop Icons23:14 Cyndi Lauper vs. Madonna: A Media Comparison24:34 Lady Gaga's New Single: Campy Fun27:13 Travel Chaos: New EU Rules28:56 UK Jet Fuel Crisis: A Discussion32:32 Remembering Prince: A Legacy40:47 Prince's Concert Memories and Impact45:48 Outro

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Ep 91 - Was Cyndi Bigger Than Madonna in The 80s?

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