Why Is This So Hard For You?

Episode 148 moves from slick ’80s British pop into sprawling modern prog before the category round uncovers an original version hiding in plain sight—and one of the strangest records ever to become a legitimate hit.

Jonathan opens with Curiosity Killed the Cat, bringing polished UK pop, funk, soul, and that unmistakably stylish late-’80s production. Curtis follows with a live Porcupine Tree performance, where atmospheric textures gradually give way to heavier guitars, shifting dynamics, and the kind of slow-building progressive rock intensity that makes the live version feel like an event rather than just another performance.

For the category songs, Jonathan brings Original Version with Neil Diamond, going back to the surprisingly subdued beginning of a song that would later become much better known in an entirely different form. Curtis then unveils America, Explain Yourself, featuring Dickie Goodman and a novelty record so thoroughly rooted in a particular moment of 1970s pop culture that its chart success may require a congressional investigation.

British ’80s cool, Porcupine Tree in full live-prog mode, Neil Diamond before the reggae makeover, and a record that only America could have made into a hit—Episode 148 gets progressively harder to explain as it goes.

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.

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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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.

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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.

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.

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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.

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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.

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.

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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.

Episode 144 starts with another trip to the movies, moves into some serious instrumental muscle, and eventually reaches a recording that forces Curtis to reopen the Sonic Holocaust file.

Jonathan continues his soundtrack streak with Billy Joel, digging up a movie song that sounds unmistakably like him while living a little outside the part of his catalog most people know. Curtis follows with Snarky Puppy, where the grooves get heavier, the musicianship gets ridiculous, and keeping track of exactly what everyone is doing becomes part of the fun.

Then the categories take over. Jonathan introduces Needed The Money, featuring Robbie Dupree in a musical situation that raises a very reasonable question: How did this happen? Curtis counters with Sonic Holocaust, turning to an enormously famous actor who decided that conquering movies and comedy apparently wasn’t enough.

A movie-song curiosity, modern jazz-fusion fireworks, a suspicious career choice, and one celebrity recording that must be heard to be believed—Episode 144 rewards anyone willing to follow the show down a few strange musical side roads.

Curtis Gross is a self-employed video editor.

Jonathan Workman is an adult learning consultant based in Wichita, KS.

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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.

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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.

Episode 143 gets smooth, cinematic, and increasingly questionable as Curtis brings some late-night jazz-pop atmosphere, Jonathan continues digging through movie soundtracks, and the category round moves from grown-up soul to an aging crooner reaching for arena-rock relevance.

Curtis opens with Michael Franks, bringing his trademark blend of jazz, soft rock, understated grooves, and impossibly laid-back vocals. It’s sophisticated, nocturnal music that sounds like it should come with dim lighting and a drink menu. Jonathan keeps his movie-song streak going with Tom Johnston, finding another overlooked soundtrack cut that brings some unmistakable Doobie Brothers-adjacent muscle to the big screen.

For the category songs, Curtis brings Put The Kids To Bed with Average White Band—slow, soulful, and subtle enough that the category name pretty much explains what happens next. Jonathan then introduces Desperate For Relevance, as Engelbert Humperdinck takes on a huge Journey anthem in an attempt to bring a little arena-rock drama into the world of traditional pop.

Michael Franks after dark, a soundtrack deep cut, AWB setting the mood, and Engelbert reaching for the cheap seats—Episode 143 goes from sophisticated to wonderfully unnecessary in record time.

Curtis Gross is a self-employed video editor.

Jonathan Workman is an adult learning consultant based in Wichita, KS.

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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.

Episode 142 keeps Jonathan’s movie-song streak rolling, then jumps headfirst into Van Halen before the category round brings weed smoke, unlikely collaborations, and one massive power ballad that somehow never reached No. 1.

Jonathan starts with Stephen Bishop and another trip into the world of movie soundtracks, this time pulling a smooth, overlooked performance from Tootsie. It’s polished early-’80s soft rock with cinematic sheen, sophisticated songwriting, and Bishop’s unmistakably warm vocal style—the kind of soundtrack cut that deserves a life outside the movie. Curtis follows with Van Halen, digging into the darker, tougher side of the band with Eddie Van Halen’s unmistakable guitar attack, shifting rhythms, and full-band swagger.

For the category songs, Jonathan introduces Up In Smoke with Willie Nelson and Snoop Dogg—a collaboration so inevitable it almost feels like it should have happened years earlier. Curtis then brings #1 In Our Hearts with Eric Carmen, spotlighting a towering soft-rock ballad that became a classic even without ever claiming the top spot on the charts.

Movie-soundtrack polish, Van Halen muscle, Willie-and-Snoop chemistry, and Eric Carmen going full emotional nuclear strike—Episode 142 has a little bit of everything.

Curtis Gross is a self-employed video editor.

Jonathan Workman is an adult learning consultant based in Wichita, KS.

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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.

Episode 141 starts in classic-rock territory, takes a cinematic singer-songwriter turn, and then heads directly into two category songs that may test everyone’s patience in very different ways.

Curtis opens with Styx and a key moment in the band’s evolution—the first album to feature Tommy Shaw. The track begins almost like a straight singer-songwriter piece, restrained and melodic, before gradually opening up into the harmonies, guitars, theatricality, and full-scale Styx energy that would become such a big part of the band’s sound.

Jonathan follows with James Taylor and a soundtrack song that proves even a movie assignment can still sound unmistakably like James Taylor. It’s warm, reflective, and quietly emotional, with the kind of understated storytelling and musicianship that can easily get overlooked when people stick to the familiar hits.

For the category songs, Curtis introduces No One Asked For This with Brad Paisley and LL Cool J, revisiting their much-discussed attempt to tackle race relations by combining country and hip-hop in one very unusual collaboration. Jonathan then returns to Burnt To A Crisp with Bob Seger, taking on a classic-rock staple that decades of radio, movies, bars, weddings, and probably every jukebox in America have thoroughly cooked.

Styx building from acoustic restraint to full arena-rock force, James Taylor going cinematic, an unlikely country-rap experiment, and Bob Seger served extra crispy—Episode 141 covers a lot of musical ground and leaves a little smoke behind.

Curtis Gross is a self-employed video editor.

Jonathan Workman is an adult learning consultant based in Wichita, KS.

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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.

Episode 140 gets smooth, sophisticated, and then deeply questionable as Curtis and Jonathan move from polished West Coast AOR into expansive jazz atmosphere before the category songs start raising eyebrows.

Curtis opens with Bill Champlin, bringing soulful vocals, studio-musician polish, and that sweet spot where soft rock, yacht rock, and blue-eyed soul all start sharing the same expensive microphone. Jonathan follows with Pat Metheny and Lyle Mays, adding lyrical jazz fusion, spacious textures, and the kind of instrumental beauty that makes you stare thoughtfully out a window even if you are just sitting in traffic.

For the category songs, Curtis brings There Should Have Been An Intervention with Frank Sinatra and Bono, a pairing that feels like someone should have gently stepped between the legends and the recording booth. Jonathan then introduces I See What You Did There with Dave Barnes, spotlighting a song packed with pop music references and clever little lyrical winks.

Champlin soul, Metheny/Mays elegance, Sinatra/Bono confusion, and Dave Barnes wordplay—Episode 140 is smooth, smart, and just weird enough to keep everyone honest.

Curtis Gross is a self-employed video editor.

Jonathan Workman is an adult learning consultant based in Wichita, KS.

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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.

Episode 139 moves from Southern rock atmosphere into silky adult-contemporary sophistication before the category songs take a hard turn into overplayed-radio exhaustion and late-’80s redemption.

Jonathan opens with Atlanta Rhythm Section, bringing melodic classic rock, polished Southern groove, and the kind of overlooked album-cut energy that fits perfectly in the deep cuts lane. Curtis follows with Al Jarreau, adding warm vocals, smooth jazz-pop elegance, and enough musical sophistication to remind everyone that “easy listening” does not mean “easy to sing.”

For the category songs, Jonathan brings Burnt To A Crisp with The Righteous Brothers, revisiting a legendary record that has been played, covered, re-played, re-covered, and emotionally slow-danced into dust. Curtis then brings Remember This One Instead with Cutting Crew, making the case that there is more to the band than the one massive hit everyone immediately thinks of.

Southern polish, Jarreau-level vocal class, a gloriously overcooked classic, and a better Cutting Crew conversation—Episode 139 is smooth, familiar, and just roasted enough.

Curtis Gross is a self-employed video editor.

Jonathan Workman is an adult learning consultant based in Wichita, KS.

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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.