The 500 with Josh Adam Meyers

Episode 145: Steely Dan – “Aja” (1977) w/ Big Jay Oakerson
August 27, 2025

Episode Overview

In this episode, comedian Josh Adam Meyers and special guest Big Jay Oakerson dive into Steely Dan’s classic album Aja—Rolling Stone’s #145 on the “500 Greatest Albums” list. With the trademark mix of irreverence, honest music appreciation, and comic banter, Josh and Jay explore the legacy and sound of Steely Dan, especially the band’s association with “yacht rock.” The conversation roams from the album’s famously meticulous production and jazz-pop style to personal stories about growing up with this music, as well as the appeal—and mockery—of the yacht rock aesthetic. The episode also features lively tangents, reflections on musical tastes, and plenty of jokes, blending insight and comedy for both diehard Steely Dan fans and the uninitiated.

Key Discussion Points & Insights

1. Big Jay’s Eclectic Taste & Yacht Rock Love

• Big Jay’s Past Selections: Jay has discussed everything from Cyndi Lauper to Def Leppard, Jethro Tull, and Red Hot Chili Peppers on the show. Josh remarks:

  “You might have the most eclectic… you coined the term California Queef Rock.” (08:31)

• Yacht Rock Roots: Jay explains his deep connection to yacht rock, crediting his mother’s musical tastes driving at night in the '80s as an early influence.

  "That's back-on-my-mom's-car music. So it's soothing in that regard.” (16:50)

• Silk Shirt Rock: Jay preferred his own term before yacht rock took hold:

  “I used to call it Silk Shirt Rock...all these guys wearing silk shirts...the beard, the hair, the music seems so corny, but you know they were smashing.” (18:25)

2. What Makes Steely Dan Unique

• Studio Band or Live Group? The hosts discuss Steely Dan’s persona as studio perfectionists—rarely touring, and more jazz nerds than rock stars.

  "They don’t even tour, like, at all… they’re just studio guys." (20:22)

• The Perfection Factor: The duo marvel at Steely Dan’s ability to assemble superstar musicians for each track.

  “They literally would pull in perfect people for every single instrument on what they felt the vibe of the song was.” (29:33)

3. Aja’s Reputation vs. Personal Preference

• Is Aja Overrated? The standard critical take is that Aja is Steely Dan’s best, but both hosts admit they have personal favorites elsewhere in the catalog.

  “Out of the other two records we’ve listened to, I enjoyed those way more than I enjoyed this one." (27:07) — Josh
  “This doesn't have… not for me, not for my time, but a lot of people, I understand that completely.” (50:16) — Jay

4. Track-by-Track Highlights

• Black Cow: Noted for its hip-hop samples and smooth, melancholy vibe.

  "Heavily, heavily sampled song in hip hop. Uptown Baby… MF Doom, Beyoncé, Tone Lōc...” (30:08–33:11)

• Aja (the title track): Noted for mythic, sensual lyrical inspiration, and Steve Gadd’s legendary drumming—performed in one take.

  “This is literally one of the greatest drum performances ever.” (36:19)

• Peg: Celebrated for Michael McDonald's iconic “back to you” harmonies and extensive sampling.

  [Plays McDonald’s isolated vocals:]
  "Can we give you more, Michael? You’re a good voice, dude." (52:03)

• Deacon Blues: The showstopper for Jay, tied to personal memories and inside jokes (“Deacon Boobs” as a road-trip parody song).

  “I always have a soft spot for [Deacon Blues]...it catches me, a much darker parody song than me and you would sing when there’s no cameras.” (44:34)

5. The Yacht Rock Genre – Corny or Sexy?

• Rebranding Yacht Rock: Jay resists the genre’s reputation as old-people-on-a-boat music:

  “To me, it’s sexier than that… it’s these guys wearing silk shirts going out and, like, getting the chicks that love guys with long hair and silk shirts." (21:12)

• “Ambrosia” and Silk Shirt Vibes:

  “My mind keeps coming back to Ambrosia… They really encapsulate that thing. The music is so queefy, but that main guy was cool...curly, kind of long...looked like John Holmes almost.” (71:24)

6. Sampling, Musical Influence & Legacy

• Who’s Sampled More? The hosts debate the most-sampled acts, landing on James Brown and The Winstons, but noting Steely Dan’s huge hip-hop impact.

  “If we consider all genres… the highest ever: James Brown—617." (44:02)

• Steely Dan’s Niche Status: They discuss how the band’s lack of touring may have kept them "niche," but their influence is enduring:

  “They’re the godfathers, unwittingly, of a genre… and it’s macaroni and cheese—warm as f***.” (63:16)

Notable Quotes & Memorable Moments

• On Steely Dan’s Studio Musicianship:

  “They don’t even tour, they’re just studio guys… they just make albums in the studio and put them out…” — Big Jay (20:22)

• Jay’s Ideal ‘70s Life:

  “If you could be born at a different time… whatever would have made me a formidable teenager straight through the ‘70s… I would have really enjoyed…” (72:28)

• On Genre Crossover:

  “I’m into rock and roll… I don’t look weird if I go to a Slipknot concert dressed that same way somehow.” — Jay (13:47)

• Josh on discovering the depth in yacht rock:

  “After talking to Nick from the Goddamn Comedy Jam, you realize how complicated this music is… speed this up, this is progressive rock.” (19:03)

• Deacon Blues Road Parody:

  “They call Alabama the Crimson Tide, call me Deacon Boobs made us laugh… I don’t even have these kind of laughs anymore…” — Jay (44:57)

• On the appeal of yacht rock:

  "Warm as f***...it's me sitting in the back of a car, that music...I get a night where I don't have to just lay in bed..." — Jay (63:42)

Important Timestamps

• Yacht Rock & Silk Shirt Origins: 16:50 – 18:25
• Steely Dan’s Unique Approach: 19:18 – 21:12
• Aja vs. Other Albums: 27:07 – 29:09
• Track Analysis – Black Cow: 30:08 – 33:11
• Track Analysis – Aja: 34:03 – 36:19
• Track Analysis – Peg & Michael McDonald Vocals: 51:26 – 52:39
• Jay’s ‘Deacon Boobs’ story: 44:34 – 47:30
• Who Samples Whom / Hip-Hop Connections: 38:10 – 44:13
• Closing Thoughts on Yacht Rock & Album Legacy: 63:07 – 74:56

Final Thoughts & Summary

• Album Elevator Pitch (Big Jay):

  "You're gonna get three songs. It's gonna let you know immediately if you are into Steely Dan’s vibe or not. Those three songs are Steely Dan songs. A mega chorus… studio music so they make it. Steely Dan fills the speakers with sound." (69:02)

• On Aja’s Place in Steely Dan’s Legacy: The hosts agree that while Aja is highly acclaimed, their personal favorites might lie elsewhere—yet Aja remains a monument to musicianship, lush studio production, and Steely Dan's unique fusion of jazz, pop, and rock.

• Big Jay's Yacht Rock Champion: Ambrosia, with Steely Dan right up there as the genre's “godfathers.” (71:24)

Where to Find the Hosts

• Big Jay Okerson:

  • @bigjokerson on YouTube and all socials
  • Tour dates at BigJComedy.com
  • Podcasts: Legion of Skanks, The Bonfire, Story Wars

• Josh Adam Meyers:

  • @joshadammeyers on all socials
  • Show info at The500Podcast.com

Up next:
Episode 146 – N.W.A., Straight Outta Compton

For New Listeners

This episode blends comic riffing with genuine musical insight. If you’re new to Steely Dan or looking for an intro to Aja, expect a mix of irreverence, nostalgia, and nuanced appreciation—plus a strong case for giving yacht rock a second chance.