Life is too short to curate anemic musical tastes. Classic rock and pop radio plays the same batch of focus-tested songs ad nauseam. Even stations that claim to "play everything" (stations that begin with male personal pronouns) offer only slightly larger playlists.
We wondered, "Why is it so hard for people to find new songs by their favorite artists? Or better yet, find a new genre of music altogether to explore." Hence, the Why Is This So Hard For You podcast was born.
🎧Episode 147: Keith Jarrett Beauty, Style Council Sophisti-Pop & A Duet Nobody Saw Coming
Episode 147 moves from lyrical jazz to sharp ’80s British pop before the category round digs up a once-enormous hit and an unlikely celebrity collaboration that demands an explanation.
Curtis opens with Keith Jarrett, bringing the spacious melodies, expressive piano, and understated beauty that made his European quartet such a distinctive corner of modern jazz. Jonathan continues his run through UK ’80s music with The Style Council, where Paul Weller trades punk urgency for soul, jazz, pop, and sophisticated arrangements without losing his songwriting bite.
For the category songs, Curtis introduces So Big It Disappeared, revisiting Bo Donaldson and the Heywoods and a record that was absolutely massive in the ’70s but has somehow faded from everyday rotation. Jonathan then offers My Apologies, featuring Dolly Parton and Sylvester Stallone in a pairing that immediately raises several questions—most of which are probably better answered by simply hearing it.
Beautiful jazz, British sophisti-pop, a forgotten blockbuster, and Dolly Parton sharing a microphone with Rocky—Episode 147 takes another perfectly reasonable trip through the less reasonable corners of music history.
Curtis Gross is a self-employed video editor.
Jonathan Workman is an adult learning consultant based in Wichita, KS.
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The intro music is the first 30 seconds of the Ornette Coleman tune "Song X" fed into AI software that attempts to output the song to a solo piano transcription. The outro music is the first 30 seconds of Sonny Rollins' version of the tune "St. Thomas" fed into the same software.
26 Oct 2026
🎧Episode 146: Hue and Cry Soul-Pop, Prefab Sprout Sophistication & A Halloween Detour
Episode 146 starts with two beautifully crafted pieces of British pop before the category round takes us from seasonal weirdness to one of the stranger stories behind a late-blooming hit.
Jonathan opens with Hue and Cry, bringing blue-eyed soul, sophisticated pop, and the kind of sharp ’80s production that rewards a closer listen. Curtis follows with Prefab Sprout, where Paddy McAloon’s songwriting and Thomas Dolby’s production meet in that unmistakable blend of sophisti-pop, melodic detail, and studio craftsmanship that somehow sounds both very 1985 and completely timeless.
For the category songs, Jonathan introduces ’Tis The Season, but this time the season is Halloween—and his selection proves that holiday records can get strange well before Christmas arrives. Curtis then brings Dead Band Walking, featuring Sheriff and one of those music-industry stories where the hit showed up after the band had already essentially ceased to exist.
Sophisticated pop, Prefab Sprout perfectionism, a bizarre seasonal diversion, and a hit single that arrived almost too late to matter—Episode 146 is full of songs with more going on behind them than you might expect.
Curtis Gross is a self-employed video editor.
Jonathan Workman is an adult learning consultant based in Wichita, KS.
---
Make sure you are subscribed to Why Is This So Hard For You. Type Why Is This So Hard For You in your podcast provider, hit that subscription button, and leave us a five-star review. This will make it easier for other podcast listeners to find the podcast.
---
The intro music is the first 30 seconds of the Ornette Coleman tune "Song X" fed into AI software that attempts to output the song to a solo piano transcription. The outro music is the first 30 seconds of Sonny Rollins' version of the tune "St. Thomas" fed into the same software.
19 Oct 2026
🎧Episode 145: Gino Vannelli Meets Leonid & Friends, Deacon Blue Deep Cuts & A Very Dark Top 40 Hit
Episode 145 starts polished, sophisticated, and very musical—then the category round takes a turn that gets considerably more disturbing.
Curtis opens with Leonid & Friends teaming up with Gino Vannelli, bringing big arrangements, immaculate playing, and the kind of studio-musician precision that lives right in the show’s wheelhouse. Jonathan follows with Deacon Blue, adding literate pop-rock, blue-eyed soul, and an overlooked late-’80s cut with plenty of character beneath the polish.
For the category songs, Curtis introduces Tastes Like Chicken, and the less said beforehand, the better. Let’s just say The Buoys managed to turn one of pop music’s strangest stories into an actual hit record. Jonathan then brings #1 In Our Hearts with Michael Jackson, spotlighting a song so iconic, so instantly recognizable, and so culturally enormous that it feels almost impossible that it never reached No. 1.
Virtuoso polish, smart Scottish pop, one deeply unsettling novelty of the charts, and Michael Jackson somehow missing the top spot—Episode 145 covers a lot of ground, and some of it is definitely not for the squeamish.
Curtis Gross is a self-employed video editor.
Jonathan Workman is an adult learning consultant based in Wichita, KS.
---
Make sure you are subscribed to Why Is This So Hard For You. Type Why Is This So Hard For You in your podcast provider, hit that subscription button, and leave us a five-star review. This will make it easier for other podcast listeners to find the podcast.
---
The intro music is the first 30 seconds of the Ornette Coleman tune "Song X" fed into AI software that attempts to output the song to a solo piano transcription. The outro music is the first 30 seconds of Sonny Rollins' version of the tune "St. Thomas" fed into the same software.
Reach and audience
Public platform figures. Ratings count people who left a rating, not total listeners.
Apple Podcasts (US)
5.0 / 5
3 ratings
Spotify
5.0 / 5
5 ratings
Podcast Authority Score: 40 / 100
A composite of feed quality, social presence, YouTube performance and engagement. Read the methodology.
Quality
55
Social presence
0
YouTube
0
Engagement
60
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Guest appearances
Books guests
Based on episode analysis; this does not confirm that the show is currently accepting guests.
Questions about Why Is This So Hard For You?
Who hosts Why Is This So Hard For You??
Curtis Gross and Jonathan Workman host the show. Published by witshfy.
How often do new episodes come out?
The show publishes weekly, based on its RSS feed.
Does Why Is This So Hard For You? take guests?
Yes. Guests have been identified in episode analyses.
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