🎧 Episode 109: Classic Chicago, Alt-Pop Quirk & Covers with a Message

This week Curtis and Jonathan bounce between polished classic rock, left-of-center pop, and a double dose of covers that each take very different approaches.Curtis opens with a smooth, late-era selection from Chicago, leaning into their more reflective, songwriter-driven side. Jonathan follows with a characteristically quirky pick from They Might Be Giants, bringing wit, odd angles, and unmistakable personality into the mix.Jonathan also takes the reins for The Deep Cut State, where we once again begin connecting dots, noticing patterns, and asking questions we probably shouldn’t—purely for research purposes, of course.The category songs keep things soulful and thoughtful. Curtis brings a Cover from Blood, Sweat & Tears, reworking a timeless standard with weight and intention, while Jonathan counters with another Cover, this time from Livingston Taylor, offering a warm, understated reinterpretation rooted in melody and feel.Classic bands, clever detours, conspiracy vibes, and covers that actually mean something—this episode hits all the familiar pressure points.Audio note: Curtis’ microphone went rogue during this recording session. It’s been fixed going forward.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.