Planet Money: PM Does a Pop Culture Draft — 1999 Edition

Podcast: Planet Money (NPR)
Episode Date: December 17, 2025
Hosts: Kenny Malone, Waylon Wong, Jeff Guo
Episode Theme: In this special bonus episode, the Planet Money team holds a playful but insightful “pop culture draft,” using an NBA-style draft format to pick their ultimate “Planet Money 1999 pop culture team.” Each pick must connect to both 1999’s pop culture and Planet Money’s focus on the economy—sometimes in surprising ways. The hosts debate, defend, and elaborate on their picks in three rounds: Movie, Song, and Wild Card, discussing both the nostalgia and the economic currents beneath the pop artifacts.

Main Theme and Purpose

The episode is a mix of fun, nostalgia, and economic analysis:

• Purpose: To draft the most “Planet Money” pop culture lineup of 1999, choosing artifacts (movies, songs, wildcards) that exemplify how economic and societal trends are manifested in culture.
• Unique Angle: Each selection is justified through the lens of economic reasoning, business trends, market disruption, or some aspect of financial or social infrastructure.
• Listener Involvement: The ultimate winner is chosen by the Planet Money audience via vote.

Episode Structure & Key Discussion Points

1. Draft Format and Rules [04:04]

• Draft Structure: Three rounds per person—each must pick:
  • One movie (from 1999’s top 100 domestic grossing films)
  • One song (from the Billboard Hot 100)
  • One “wild card” (any pop culture artifact from 1999)
• Order Determination: Snake order is set by spinning a color wheel, maximizing fairness and drama.
• Judgment Criteria: The “Planet Money-iest” connection—does it tie back clearly/cleverly to the economy?
• Aims: Elbowing fun and nostalgia with a competitive, yet friendly, spirit.

2. Hosts’ 1999 Contexts [07:30]

• Personal Contexts:
  • Kenny: Age 15, obsessed with Star Wars, not allowed to see R-rated movies.
  • Waylon: Age 17, senior in high school, remembers music and school orchestra performing Star Wars.
  • Jeff: 10 years old, “barely had a childhood,” jokes about being “reconstituted” from powder form.

The Draft: Picks and Economic Logic

Round 1: Movie Picks

Waylon Wong — The Insider [11:14]

• Why: “Very clearly about business… it is my favorite movie of all time.”
• Economic Connection: Corporate whistleblowing, journalism vs. corporate interests, merger pressures (CBS/Westinghouse case), cyclic corporate influence on media.
• Memorable Quotes:
  • “Lawyer me. Are you gonna finesse me?” [13:19, Christopher Plummer as Mike Wallace]
  • “If you get mad and you get curious, that's actually a very potent recipe for doing some journalism.” [13:07]
• Tone: Passionate and personal.

Kenny Malone — The Blair Witch Project [14:13]

• Why: “It is still one of the most profitable movies ever made.”
• Economic Connection:
  • Micro-budget film with massive profits (~70k to $248M = 250x return)
  • Sparked a new horror business model (Blumhouse model: low-cost, high-reward), directly cited by Jason Blum.
  • Viral marketing before the concept of “virality” existed.
• Memorable Quotes:
  • “How is Blair Witch Project not a Planet Money movie?” [17:01]
• Notable Moment: Discusses physical reactions to the film and the impact of its found-footage style.

Jeff Guo — Pokémon: The First Movie – Mewtwo Strikes Back [20:16]

• Why: “This was the gateway drug for a lot of people for anime and Japanese culture.”
• Economic Connection:
  • Cross-media synergy (“omnimedia”): games, cards, TV, merchandise, making Pokémon a global cultural and economic juggernaut.
  • Intellectual property as export—early sign of cultural globalization and “K-popification” of entertainment.
  • Outsized box office performance, beating adult “prestige” titles.
• Notable Quote:
  • “Culture, intellectual property—a big deal, a big economic deal. And it comes from all over.” [21:49]

Round 2: Song Picks

Jeff Guo — Backstreet Boys: “I Want It That Way” [24:35]

• Economic Connection:
  • “Height of the boy band economy.”
  • Illustrates “comparative advantage” in labor economics—the right band member for the right musical skill.
  • Lyrics as semiotically unstable: confusion (“What does ‘I Want It That Way’ actually mean?”) reflecting modern uncertainty and complexity in markets/media.
• Memorable Quotes:
  • “You can really see an illustration of the concept of comparative advantage… each person should do what they are best at compared to their own skills.” [26:25]
  • “These lyrics… they're very semiotically open, right? Like epistemologically unstable.” [29:23]
• Fun: Serious econ theory applied humorously to manufactured pop.

Kenny Malone — Destiny's Child: “Bills, Bills, Bills” [30:28]

• Why: “An ode to financial responsibility.”
• Economic Connection:
  • Lyrics about financial boundaries, credit, and personal responsibility in relationships.
  • Reflects the rising importance (and pitfalls) of credit cards in late-90s America.
• Memorable Quotes:
  • “Most 18 year olds are not thinking about FICO scores. This is amazing.” [31:41]
  • “Bills, bills, bills would not have made sense 10 years prior.” [32:18]

Waylon Wong — TLC: “No Scrubs” [33:01]

• Why: “It speaks to broader dynamics we see in marriage rates, especially across socioeconomic classes.”
• Economic Connection:
  • Scrubs as “deadbeat” partners—a metaphor for growing economic inequality and its social consequences, including shifting marriage patterns.
  • Gender roles, labor, and rising rates of women staying single rather than “marrying down.”
• Memorable Quotes:
  • “I think this song speaks to broader dynamics… marriage rates have been going down as you go down the income ladder.” [34:02]
  • Compares “risk avoidance” (No Scrubs) to the “bad outcome” (Bills, Bills, Bills) [36:21]
• Notable: Continued relevance, even 25 years on.

Round 3: Wild Card Picks

Waylon Wong — House Hunters (TV Show debut) [37:47]

• Why: “Really changed our entire relationship as a culture with one of the most important sectors of the economy.”
• Economic Connection:
  • Fostered the national obsession with real estate, home ownership, and “Zillow stalking.”
  • Influenced design trends and the “American dream” narrative of ownership.
  • “I think without House Hunters, you might not get Zillow stalking, you might not get this obsession with… judging people’s aesthetic choices.” [38:13]
• Notable Moment: Discussion of mortgage rates in the 1990s and cultural obsession with open floor plans, judging people's taste, etc.

Kenny Malone — Whoopi Goldberg’s commercial for Flooz.com [40:09]

• Why: “A commercial for a company that I think you could argue just sort of is the dot com bubble.”
• Economic Connection:
  • Flooz.com as a “digital currency” before crypto, but built for online shopping (early digital payment experiments).
  • Symbolic of dot-com excess, fads, and ultimate bust (bankruptcy after a credit card scam).
  • Direct echo with recent crypto craze and celebrity endorsements: “There’s Larry David, like, promoting crypto…”
• Memorable Quotes:
  • “So I draft not the whole dot com bubble, right? But I do… Whoopi Goldberg in a flooz commercial telling people they're old and should buy digital currency.” [42:45]
  • “You flew. You lose. That's what happened.” [44:57—Waylon Wong’s pun]

Jeff Guo — Napster (the music file-sharing platform) [45:20]

• Why: “In a way, I’m picking all of the songs. The sum total of songery in 1999 was on Napster.”
• Economic Connection:
  • Fundamentally disrupted the music industry’s economics, leading to iPod, streaming, collapse of the traditional recording industry, and new touring-oriented artist models.
  • Democratized access to music and music production (pirated software enabled a generation of bedroom producers/DJs).
  • “Napster allowed us to seize the means, both of production and reproduction.” [47:21]
• Notable Quotes:
  • “Without Napster, we would not have the ipod. Without Napster, we wouldn't have Spotify.” [45:11]

Audience Voting and Winner Reveal

• Voting: Listeners (Planet Money+ supporters) voted for who drafted the best Planet Money 1999 pop culture team.
• Result:
  • Winner — Waylon Wong (by a landslide)
  • 2nd place — Jeff Guo
  • 3rd place — Kenny Malone (“I do blame Flooz for that. I think I tanked it with Flooz.” [54:14])
  • Waylon’s Victory Quote: "Thanks so much for believing in me and my picks… I hope maybe I inspired some people to go watch [The Insider] who haven't seen it before." [53:57]

Notable Quotes & Fun Moments

• On Drafting Strategy:

  • “This is the sportiest I’ve ever been. I’ve never done such a sports-adjacent thing.” — Waylon Wong [03:33]
  • “This is giving me a lot of insight into what your potential picks might be.” — Jeff Guo [08:54]

• Cultural/Economic Theory Mashups:

  • “Comparative advantage just means each person should do the thing that they are best at compared to their own skills… If you look at the song…” — Jeff Guo, applying econ theory to boy bands [26:25]
  • “It feels free.” — Waylon Wong, on streaming in the post-Napster era [46:21]

• Pop Criticism & Satire:

  • “Fight Club really represents the pinnacle of Gen X culture where, oh my god, the worst thing that could happen to me in life is that I have a regular degular job.” — Jeff Guo [49:57]

• Callbacks & In-Jokes:

  • “You flew, you lose.” — Waylon Wong on the fate of Flooz.com [44:57]
  • “Lawyer me. Are you gonna finesse me?” — Channeling Insider’s Mike Wallace [13:19]

Timestamps for Important Segments

• [04:04] — Draft format/rules explained
• [07:30] — Hosts describe their 1999 selves
• [11:14] — 1st movie picks begin (The Insider)
• [14:13] — Blair Witch Project pick & horror business discussion
• [20:16] — Jeff's Pokémon Movie pick & IP global export analysis
• [24:35] — Song picks commence: "I Want It That Way" and labor econ
• [30:28] — Bills, Bills, Bills: credit, responsibility, relationships
• [33:01] — No Scrubs: socioeconomic analysis of marriage and attraction
• [37:47] — Wild card picks start: House Hunters and the home buying obsession
• [40:09] — Flooz.com, dot com bubble, and precursors to crypto fads
• [45:20] — Napster: the music industry turned upside down
• [53:57] — Winner announcement, with Waylon thanking supporters

Recap of Winners’ Teams

Waylon Wong

• Movie: The Insider
• Song: No Scrubs (TLC)
• Wild Card: House Hunters (TV show)
• Theme: Corporate whistleblowing, class & gender in relationships, the real estate dream.

Kenny Malone

• Movie: The Blair Witch Project
• Song: Bills, Bills, Bills (Destiny’s Child)
• Wild Card: Flooz.com commercial (Whoopi Goldberg)
• Theme: Micro-budget disruption, personal finance in song, the folly of dot-com get-rich-quick schemes.

Jeff Guo

• Movie: Pokémon: The First Movie — Mewtwo Strikes Back
• Song: I Want It That Way (Backstreet Boys)
• Wild Card: Napster
• Theme: Global pop culture as economic force, economic theory in entertainment, digital disruption.

Final Thoughts

• Nostalgia and Economics Collide: The episode is a clever showcase of how the economic undercurrents of an era surface through pop culture, and how analytical frameworks can offer both humor and insight into nostalgia.
• Listener Participation: The format encourages listeners to reconsider old favorites through an economic lens (and to debate what makes an artifact “Planet Money worthy”).
• Recurring Joke: Flooz.com as Kenny’s undoing and a symbol of dot-com excess; Waylon’s rage-as-journalism thesis.

Suggested Follow-Ups

• Listeners are invited to suggest a year for next season’s pop culture draft.
• Sign up for Planet Money+ for more bonus content.

For fans of Planet Money, this episode is a must-listen for fun and insight—especially for anyone who lived through (or just loves) 1999.