Summary of Ep 626 - Oil Boy (feat. Dru Montana & Lemaire Lee)

Overview of Ep 626 - Oil Boy (feat. Dru Montana & Lemaire Lee)

Matt McCusker and Shane Gillis, joined by Dru Montana and Lemaire Lee, spend most of this episode riffing on work frustrations, delivery apps, internet culture, animals, sex work, strip clubs, and the mechanics of pimping. The conversation is loose, rude, and highly comedic, with a recurring theme of men trying to survive bad jobs, weird social dynamics, and the absurdity of modern life.

Main Topics Discussed

Delivery apps and “unicycle guy” energy

• The episode opens with a story about a GoPuff delivery driver who had a bad attitude while dropping off a large case of water.
• The hosts joke about “humble lads” versus “unicycle white guys,” using the imagined unicycle rider as a symbol of smug, annoying energy.
• They compare GoPuff, DoorDash, and the difficulty of being expected to carry heavy loads for delivery work.

Quitting jobs and lying in interviews

• A big chunk of the episode is about miserable jobs, especially office work and food delivery.
• The guests share stories of quitting jobs mid-shift without telling anyone.
• They joke about inflating resumes, pretending to know Excel, and overclaiming Microsoft Office skills.
• The broader point: most jobs are soul-crushing, and interviews are built on mutual lying.

Tech, screen time, and internet overload

• The crew talks about hating phones, lowering screen time, and how addictive Reels and endless scrolling can be.
• They joke that “screen time” often includes GPS and other passive phone use, which makes the number feel even more absurd.
• There’s also talk about Facebook’s campus, tech perks, and the idea that tech jobs try to trap people with fake comfort.

Notable Stories and Running Bits

Wildlife encounters and “life-or-death” fantasies

• The conversation veers into animal attacks, including a viral-looking jaguar attack and a bison incident.
• They joke about how cool it would be to survive a dangerous animal attack on camera and become a local legend.
• A giraffe story leads into jokes about how massive and surprisingly violent giraffes can be.

Gardening, food, and freshness

• One guest talks about gardening for the first time and growing things like okra, onions, zucchini, green beans, tomatoes, basil, mint, and garlic.
• The group discusses how much better homegrown produce tastes than grocery store food.
• They also joke about clams, oysters, and the weirdness of seafood logistics in landlocked places.

Sexual banter and “sap”

• The episode gets heavily sexual in the usual podcast way:
  • jokes about eating pussy, ass, gooch licking, and “trick trick” techniques
  • a recurring bit about “sap,” including claims about its supposed benefits
• One of the funniest long-running bits is about a woman allegedly telling someone that licking under the shaft is a “trick trick.”
• The guests also discuss the discomfort and humor around women asking to be slapped or choked during sex.

OnlyFans, “oil boy,” and pimp-adjacent work

• Dru Montana’s “oil boy” story becomes a highlight:
  • he once worked for an OnlyFans creator by setting up lights and rubbing oil into her chest on camera
  • he was paid well for it and jokingly frames it as a weird but excellent job
• The crew debates whether that counts as pimping and lands on the idea that he was basically “talent” or the “oil boy.”
• They go deeper into financial domination, strip club hustles, and the economics of sex work.

Strip clubs and sex-work chaos

• The hosts trade stories about strip clubs, Backpage, and old-school adult services.
• They talk about:
  • being tricked into paying for weird strip club experiences
  • dancers offering private attention and then trying to squeeze more money out of guys
  • the now-defunct Backpage era and how chaotic it was
  • a notorious venue called Show and Tell, known for explicit live acts and rough crowd energy
• One memorable anecdote involves a prostitute being brought to a college graduation celebration and the dancers beating the guest of honor with belts.

Pimp lore and Iceberg Slim

• The conversation turns into a more detailed joke/history lesson about pimping culture.
• They mention Iceberg Slim and the classic “bottom bitch” system, fake letters, and psychological control tactics.
• The humor comes from how methodical and ruthless the old-school pimp playbook sounds when explained plainly.

Other Recurring Jokes and Observations

Body image, height, and “sub-six” talk

• The hosts joke about height preferences, height-based wage gaps, and how many women care about a man being over six feet.
• They riff on being “sub six” and the fantasy of having Vince Carter’s dunk package while being short.

Dominance, pain, and weird intimacy

• There’s a lot of joking about who likes giving versus receiving pain during sex.
• The guests discuss what they would and wouldn’t tolerate, from scratching and biting to choking and slapping.

Announcements and Shoutouts

Tour dates and live shows

• The episode ends with a long run of live show promos for Matt McCusker, Shane Gillis, and the guests.
• They encourage listeners to buy tickets and check out upcoming tour dates, clubs, and festival appearances.
• They also shout out related podcasts and projects like:
  • Do-Rag and the Deer Tag
  • Digital Bazooka

Bottom Line

This episode is a loose, highly improvisational hang centered on:

• bad jobs and quitting them
• internet/delivery-app frustration
• sex work, strip clubs, and pimp lore
• animal attack fantasies
• gardening and food talk
• nonstop crude, competitive banter

It’s especially entertaining if you like the podcast’s usual mix of ridiculous masculinity, gross-out humor, and surprisingly specific anecdotal storytelling.