The Wayback with Ryan Sickler

Episode 102: Nate Jackson Picked Dandelions for Shoplifting
Release Date: December 11, 2025
Guest: Nate Jackson

Overview

In this lively and nostalgic episode of "The Wayback," Ryan Sickler reconnects with comedian Nate Jackson for a hilarious, heartfelt walk down memory lane. The episode explores Nate’s upbringing in Lacey, Washington, the quirks of his childhood neighborhood, his storied family church (complete with a “Tanisha clause”), run-ins and near-misses with youthful mischief—including shoplifting and a semi-illicit bike-selling enterprise—and reflections on community, temptation, and making your own history as a kid from a small town. The energy is high, the stories are vivid, and the laughs are constant.

Main Discussion Points

Nate Jackson's Career & Life Update (04:31–05:50)

• Nate’s Comedy & Acting Projects: Nate is on the "Big Dog Tour," has his own comedy/YouTube work, has collaborated musically with hip-hop legends, is acting in major TV and film projects (Netflix, "Good Fortune," "Bad Monkey," "The Paper"), and jokes, "I need a wife."
  • Quote: “Get your laugh on. You deserve to laugh this hard. And so there, there. All that is in a nutshell. I need a wife.” – Nate Jackson (05:46)

Roots in Lacey, Washington (06:01–12:52)

• Childhood Home & Neighborhood Changes:
  • Describes family home, helping his dad build things, pets, and how the property changed hands.
  • Shares how a neighbor converted the property into “Forever Young” hair salon.
  • Calls out differences in property care over time.
• Neighborhood Dynamics:
  • Discusses "Tangle Wild"—a huge development nearby that had its own social distinctions.
    • Quote: “Them kids would be like, you ain’t from Tanglewild. Like, I couldn’t go use the pool or have no summertime fun.” (08:18)
  • Recalls exclusive amenities and daycare ("Kids Choice") that seemed magical as a kid.
• Local Hangouts: Union Mills Grocery & Arcade:
  • Anecdote about the local arcade inside a brick building and avoiding older kids taking their quarters.
• The Family Church – New Life Baptist (10:09–15:12):
  • Largest Black church in South Puget Sound; details on choir, weekly activities, and the strong family and community ties.
  • Memorable “Tanisha Clause” Story:
    • Nate tells how a churchgoer with an impressive figure forced the collection process to change:
      • “People are like, we don’t need to be dealing with temptation when we’re trying to give our money to the Lord.” (14:18)
      • Ryan remarks: “They had a Tanisha clause. She changed the game. Like, they were like, this is too tempting. So now we’re just gonna do it this way, because this lady’s ass…”
  • Comment on the impact of nearby Joint Base Lewis-McChord in creating diversity in Lacey.

Growing Up: Schools, Sports, and Social Life (15:12–22:58)

• Rapid Neighborhood Growth:
  • Reflections on how the area expanded, new fields, and demographic changes.
• Schools Experience:
  • Nate describes the middle and high school setup—e.g., two football teams within one middle school (Nisqually Totems vs. Nisqually Chiefs) and their different reputations ("good kids" vs "badasses").
• High School (River Ridge):
  • Multi-campus layout—“four schools in one”—and the communal nature of student life; late-night parties, gathering at Safeway lot, and school pride.
  • Socioeconomic divisions across neighborhood subdivisions.
  • Quote: “Every school was like, whatever identity, you make it—literally.” (22:48)
• Switching Schools:
  • Sent to new schools as his mom was on the school board, making him a “first of everything.”

Shoplifting Adventure at the Capitol Mall (23:01–31:16)

• Setup:
  • Cousin’s shoplifting antics inspire Nate to try; cousin brags about "easy" scores (“new shoes, new everything”).
• Nate’s Attempt:
  • Puts on extra clothes in Bon Marche fitting room, notices a suspicious "shopper" tailing him; realizes he's being watched.
• Abort!
  • Takes off the stolen goods, but accidentally keeps a $14 t-shirt.
• Busted:
  • Security confronts him anyway—“They paraded me through there like they had caught a goddamn prize peacock” (27:44).
  • Nate’s dad negotiates at the office, pointing out Nate didn’t even intend to steal. Still, Nate gets busted thanks to his cousin’s history and association.
  • Quote:
    • “You got my kid in here, who obviously decided not to steal from you today and you mad over a $14 shirt? The kid had $30 in his pocket.” – Nate’s dad (29:47)
    • “I was a kid, man. I was black, so I did community service. I remember we had to go on the freeway and pick dandelions or something.” – Nate Jackson (30:25)
  • Reflects on racial bias (“how many little black guys are going to keep popping us”) and the reality of youthful mistakes.

Other Hilarious Youthful Mischief: Flipping Stolen Bikes (34:09–39:03)

• Bike Scheme:
  • Nate and friends would steal unlocked bikes (from “rich” neighborhoods), sell them through newspaper ads, and sometimes get a little too ambitious.
  • Anecdote about trying to sell a “futuristic” bike, getting questioned by an obvious undercover type.
  • Would hide bikes at home; mom almost supports “bike business” with tools, not realizing the source.
• Busted Again (Sorta):
  • Newspaper gets suspicious about price changes and asks for photos; fears being exposed by classified “lost bike” ads.
  • Realizes the scheme isn’t sustainable but relishes the thrill and quick cash (“no overhead!”).

Family Fish Tales & Life Lessons (39:03–41:09)

• Fishing in Backyard Pond:
  • Caught bass and even a rare, big brown trout with a Banjo Minnow.
  • Quote: “I caught a steelhead brown trout out of it…you could hit a golf ball across this body of water. This is not a lake…somebody at some point stocked it.”
  • The fish gets taxidermied, but suffers an injury when it falls on Nate’s dad (resulting in stitches).
• Reflection:
  • Even small-town, make-your-own-fun roots yield both wild stories and abiding memories.

Notable Quotes & Memorable Moments

• On new schools and making history:
  “If you’re in that school, you’re making history in there." – Ryan Sickler (22:48)
• On family, church, and community temptations:
  “Her booty was unreal…they changed [the collection]…because this lady’s ass.” – Nate Jackson / Ryan Sickler (14:18–14:29)
• On getting caught shoplifting:
  “They paraded me through there like they had caught a goddamn prize peacock.” – Nate Jackson (27:44)
• On crafting his own side hustle:
  “We just kept the ad going and we kept selling these bikes…It was a rush. Like, you’re headed out of these people’s neighborhoods with four bikes in the back of your truck.” – Nate Jackson (34:44)
• On the “Tanisha clause” at church:
  “People are like, we don’t need to be dealing with temptation when we’re trying to give our money to the Lord. So they changed it. Buckets now. No more walking up.” – Nate Jackson (14:18)

Timestamps for Key Segments

• Nate's career & current projects: 04:31–05:50
• Childhood home & property: 06:01–07:51
• Neighborhood stories & distinctions: 07:51–10:09
• Church, choir, and “Tanisha clause”: 10:09–15:12
• School spirit, sports, social life: 15:12–22:53
• Shoplifting at the mall: 23:01–31:16
• Bike theft and resale operation: 34:09–39:03
• Fishing adventures & trophies: 39:03–41:09

Episode Tone & Style

The episode is full of warmth, nostalgia, and raucous laughter, with both Ryan and Nate riffing and reminiscing in a conversational, quick-witted style. Even at its most outrageous (church drama, bike hustles), the stories land with heart and humility.

Closing & Plugs

• Nate Jackson:
  • Website for tour dates and content: natejacksoncomedy.com
  • YouTube, podcasts, music, and current acting credits (“Super Funny” on Netflix, “Good Fortune,” “Bad Monkey”).
• Ryan Sickler:
  • New Comedy Special "Live and Alive," streaming on YouTube.

This episode offers a whirlwind of genuine memories and candid laughter, perfect for fans of storytelling, comedy, and anyone who remembers growing up with big dreams in a small town.