Cop Goes to Jail Undercover on 60 Days In | Alan Oliver

Locked In with Ian Bick

Ian Bick

Society & Culture

4.8 • 745 Ratings

🗓️ 22 September 2025

⏱️ 98 minutes

🔗️ Recording | iTunes | RSS

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Summary

Alan Oliver was a police officer who did something most cops will never experience — he went undercover and spent two months inside jail on the hit TV show 60 Days In. In this interview, Alan shares what it was really like living among inmates, the danger he faced every day, and how going undercover changed the way he sees law enforcement. #60DaysIn #LockedInPodcast #CopInJail #PrisonStories #TrueCrimePodcast #UndercoverCop #LifeInJail #AlanOliver Thank you to BLUCHEW & EXPRESSVPN for sponsoring this episode: BlueChew: Visit https://bluechew.com/ and use promo code LOCKEDIN at checkout to get your first month of BlueChew FREE & pay five bucks for shipping. Express VPN: Secure your online data TODAY by visiting https://www.expressvpn.com/lockedin to find out how you can get up to four extra months. Connect with Alan Oliver: TikTok: https://www.tiktok.com/@actalan2?_t=ZP-8zrsQXmJq6I&_r=1 Instagram: https://www.instagram.com/alan_austin_oliver?igsh=MTBxa3h5azZ1ZWNyag== Hosted, Executive Produced & Edited By Ian Bick: https://www.instagram.com/ian_bick/?hl=en https://ianbick.com/ Presented by Tyson 2.0 & Wooooo Energy: https://tyson20.com/ https://woooooenergy.com/ Use code LOCKEDIN for 20% OFF Wooooo Energy Buy Merch: http://www.ianbick.com/shop Timestamps: 00:00 Is 60 Days In Real or Scripted? Behind-the-Scenes Secrets01:01 Alan Oliver’s Upbringing: Family, Childhood & Early Life02:58 Becoming a Cop: Dreams of Policing & Childhood Aspirations04:07 School Years: Bullying, Theater & Learning to Fit In09:54 From High School Graduation to Police Academy Training12:18 The Truth About Being a Cop: What They Don’t Show You19:49 Small-Town Policing: Corruption, Politics & Broken Systems23:34 Rethinking Policing: What Needs to Change in Law Enforcement28:38 Challenges of Being a Cop: The Good, Bad & Dangerous33:01 Getting Cast for 60 Days In: How Alan Ended Up on the Show37:36 Walking Into Jail as an Undercover Inmate for the First Time41:51 Social Media’s Impact: How Public Opinion Shapes Policing47:21 60 Days In Safety Concerns: Cameras, Risks & Production Secrets53:15 COs, Inmates & Learning Jail Rules to Stay Safe01:00:25 Jail Life: Food, Commissary & Daily Routine Behind Bars01:06:06 The Biggest Surprises of Living in Jail for 60 Days01:11:40 The Mental Toll: Why Alan Left Law Enforcement After the Show01:18:11 Life-Changing Takeaways & New Perspective on Policing01:24:15 Life After Policing: What Alan’s Doing Now01:30:34 How TV Shows Like 60 Days In Could Change Policing01:33:12 Final Thoughts: Lessons Learned from Jail & Policing Learn more about your ad choices. Visit podcastchoices.com/adchoices

Transcript

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0:00.0	So many people are like, oh, it's so scrimped at that show's so fake. It's not fake, dude. The inmates,
0:04.4	guards have no clue who we are. So there's, you have a legitimate chance of dying in jail
0:10.2	to film a TV show. Do you think they would let you get hurt on the show? There were certain times
0:14.7	where you felt very mistreated. What do you think was the biggest eye-opener for you doing this
0:19.7	experience? Alan Oliver was a police officer who did the unthinkable. He went undercover as an inmate on the
0:26.2	hit TV show 60 Days In. For two months, he lived among real inmates, faced gang politics, saw
0:32.9	drugs and violence up close, and risked being exposed every single day. In this episode, Alan shares the
0:39.4	most dangerous moments he faced what jail is really like when you're a cop on the inside and how
0:44.4	the experience changed him forever. Alan, welcome to Locked In, man. Thanks so much for coming
0:51.9	from Dallas to be in little old Richfield, Connecticut today.
0:55.8	Yeah, thanks for having me, brother.
0:57.5	Yeah, you said you were taking in the scenery here.
1:01.0	Again, yeah, if I could choose.
1:03.3	So I travel for work and I went to Portland and I thought that place was beautiful.
1:09.2	And I come down here and do it.
1:10.2	And I'm just like, what are these houses, man? Like being a movie or something. But yeah, this is, you'll see this in Dallas. It's like one of those Hallmark movies. That's what it is. Like, I think what happened was movie studios came down here and they just built a set of a city. And they're like, you know what? Y'all just move here. Like, we don't need it anymore.
1:28.5	Everybody just move in because it's like movie perfect. And it's the perfect weather too. Exactly. The fall time, you know, almost October, a couple weeks out from October. Yeah. Leaves are turning and stuff. The winter's pretty too when it's like a little bit of snow, not too much snow. We do get a lot of snow though, unfortunately.
1:44.9	This would be the place to live in.
1:46.5	Did you grow up in Dallas? Pretty, too. When it's like a little bit of snow, not too much snow. We do get a lot of snow, though.
1:47.7	Yeah. Unfortunately. This would be the place to live in. Did you grow up in Dallas?
1:56.9	East Texas. Yeah. It's more of like an hour and a half, two hours south of Dallas. But yeah.
1:58.0	What was your upbringing like?
	...

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