We have to talk about Woody Allen now which also means we need to talk about romance in the city. New York City, that is. Tim guides through different eras figuring out what makes love in the Big Apple a trope all its own. Annie Hall prompts us, of course, then Tim introduces The Age of Innocence and Marty which lead to talk of Edith Wharton, imagining Ernest Borgnine as any age younger than 60, Italian mothers, and Michelle Pfeiffer's immensely interesting early 90s.

Drugs and music go together like this podcast and hating on The Magnetic Fields. We as millennials remember well the lessons of D.A.R.E. (and are also very boring) but others have a more open attitude to a life of drugs. Ghostface Killah's Fishscale covers the highs and lows of drug peddling, usage, and culture and has Matt thinking, what if we 'Just Say Yes' instead? Cypress Hill and Spiritualized ask a similar question and measure the nuanced impacts of drug culture on one's health, art, bank account, and more.

The episode Tim and Matt were made for, explaining movies via Dril tweets. If you don't know Dril, go open Twitter and have yourself a reading session. We rattle off a bunch of favorites, and Tim relays how this David Lean classic is really just a Dril gem, as are The Insider and The King of Comedy. Lean, Mann, and Scorsese makes this a heavy hitter directors episode, but have they captured the spirit of their times as elegantly as Dril?

Belle and Sebastian produced a truly marvelous set of mournful yet sweet songs on If You're Feeling Sinister, a niche that they still loom over 30 years later. You might call it earnest, or even (and Matt might fight you) twee, but we call in New Sincerity. Matt and Tim talk the David Foster Wallace of it all then focus on some other breathtakingly vulnerable and poignant albums by artists in their feelings, Broken Social Scene's You Forgot it in People and Cat Powers' Moon Pix.

The movie title announces but Tim questions, are these really The Best Years of Our Lives? What makes the years best or even meaningful? How do we live out our lives as best we can? It's freshmen philosophy time, baby, but with two unrelenting cynics who, nevertheless, believe in the power of narrative. Tim brings Groundhog Day and Meet Me in St. Louis for consideration, the former with it's one-liners and latter with some immortal tunes.

Another one of those episodes where Matt pretends to know anything about electronic music. Some fun ones here though, all classics of that late-90s shooting star genre Big Beat, which is blessedly straightforward in name. Chemical Brothers make it on the Spin list with Dig Your Own Hole, and Matt talks Fatboy Slim's You've Come a Long Way, Baby and Propellerheads' Decksanddrumsandrockandroll as progenitors and exemplum of the Big Beat sound and era.

At their cores, the guys (particularly Tim) exude Dad Energy. That's surely been evident this entire podcast, but it's heightened here when they get to talk about early 19th century American history, specifically the Monroe Doctrine. See how the West was metaphorically won, or vaguely claimed, in Missing and The Mosquito Coast.

Actually okay timing here with Drake having just released a new album. Matt won't "get" that one just like he doesn't "get" Take Care...or Lana Del Ray's Ultraviolence or Father John Misty's Pure Comedy. Decade defining artists of the 2010s all, and unequivocally absent from any of Matt's personal playlists or rankings. Listen to Matt and Tim embrace their inner Abe Simpson as they ponder how they once had "it" but then "it" changed under their feet.

Dr. Strangelove is as much a movie of incredible sight gags and one-liners as it is profound political commentary. Tim and Matt share their favorites, naturally, before Tim frames the film as the more successful Twin to a similar, proximate movie. He then considers William Wyler’s Jezebel and Wes Craven’s A Nightmare on Elm Street in a similar vein, wondering what makes them more popular, successful, and ultimately lasting.

A whole host of albums on the docket in this one! Matt gives Tim the choice of two sets to be considered alongside Eric B. and Rakim’s stone-cold classic Paid in Full. (If you haven’t heard Eric B. and, especially, Rakim directly, you’ve heard them in other artists.) Tim chooses the DMX and Busta Rhymes route as Matt outlines their cases as foundational, formative acts in hip-hop.