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Dreadhead Cowboy spotted riding, flipping off horse in downtown Chicago
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Dreadhead Cowboy spotted riding, flipping off horse in downtown Chicago
2.9K views8 months ago
YouTubeCBS Chicago
LIVE REPORT: Dreadhead Cowboy rides horse on Dan Ryan Expressway
21:20
LIVE REPORT: Dreadhead Cowboy rides horse on Dan Ryan Expressway
5.1M viewsSep 21, 2020
YouTubeABC 7 Chicago
Dreadhead Cowboy rides horse on Dan Ryan Expressway
2:09
Dreadhead Cowboy rides horse on Dan Ryan Expressway
75.6K viewsSep 22, 2020
YouTubeABC 7 Chicago
'Dreadhead Cowboy' faces 3 charges after riding horse on Dan Ryan
2:12
Find in video from 00:11The Dreadhead Cowboy Rides On
'Dreadhead Cowboy' faces 3 charges after riding horse on Dan …
178.1K viewsSep 22, 2020
YouTubeWGN News
Live coverage from Sky 5: The man who has become known as the “Dread Head Cowboy” in Chicago was spotted riding his horse on the Dan Ryan Expressway this afternoon, with a motorcycle escort accompanying him. WATCH: http://nbcchi.com/Xp5dGRK | NBC Chicago
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Live coverage from Sky 5: The man who has become known as the “Dread Head Cowboy” in Chicago was spotted riding his horse on the Dan Ryan Expressway this afternoon, with a motorcycle escort accompanying him. WATCH: http://nbcchi.com/Xp5dGRK | NBC Chicago
74.2K viewsSep 21, 2020
FacebookNBC Chicago
Dreadhead Cowboy spotted riding, flipping off horse in downtown Chicago
0:32
Dreadhead Cowboy spotted riding, flipping off horse in downtown Chicago
8 months ago
CBS NewsCBS Chicago Team
The man who has become known as the “Dread Head Cowboy” in Chicago was spotted riding his horse on the Dan Ryan Expressway this afternoon, with a motorcycle escort accompanying him. Head to our link in bio for live coverage. | NBC Chicago
0:26
The man who has become known as the “Dread Head Cowboy” in Chicago was spotted riding his horse on the Dan Ryan Expressway this afternoon, with a motorcycle escort accompanying him. Head to our link in bio for live coverage. | NBC Chicago
213.9K viewsSep 21, 2020
FacebookNBC Chicago
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Dreadhead Cowboy spotted riding, flipping off horse in downtown Chicago
8 months ago
MSNCBS Chicago
0:32
Dreadhead Cowboy spotted riding, flipping off horse in downtown Chicago
8 months ago
CBS News
0:32
Give me some land in Chicago and yall won’t have to worry about me riding in the city ever again | Dreadhead Cowboy
6.2K views7 months ago
FacebookDreadhead Cowboy
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‼️CHICAGO ‼️ WE GOT A NEW HORSE 💪🏽 NOW WHAT WE GONE NAME HIM | Dreadhead Cowboy
7.1K views7 months ago
FacebookDreadhead Cowboy
0:51
**Chicago's Dreadhead Cowboy Arrested After Riding Horse On Dan Ryan Expressway Today** ⬇️ DETAILS ⬇️ CHICAGO (WLS) - - Adams Hollingsworth, also known as the Dreadhead Cowboy, did a Facebook LIVE post as rode down the expressway. In another post earlier on his Facebook page he wrote, "we focus on kids lives matter this gone keep happening' and told his followers he was going live at 4 p.m., saying, "y'all don't wanna miss this I promise." Hollingsworth and his supporters said the ride was meant
3.8K viewsSep 21, 2020
FacebookPreston Phillips
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Only person in Chicago got a service horse | Dreadhead Cowboy
57.8K views11 months ago
FacebookDreadhead Cowboy
0:44
Damn I thought I made it back to Chicago | Dreadhead Cowboy
25.5K views7 months ago
FacebookDreadhead Cowboy
Dreadhead Cowboy denies animal cruelty allegations
2:44
Find in video from 00:08Dreadhead Cowboy's Call for Help
Dreadhead Cowboy denies animal cruelty allegations
22.3K viewsSep 25, 2020
YouTubeABC 7 Chicago
1:56
Dan Ryan Expressway horse ride brings attention to investment in Chicago's children
3.6K viewsSep 23, 2020
YouTubeABC 7 Chicago
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Prince meet Chicago for the first time | Dreadhead Cowboy
7K views7 months ago
FacebookDreadhead Cowboy
0:27
Very peaceful but where am I let’s see who really kno Chicago | Dreadhead Cowboy
12.1K views5 months ago
FacebookDreadhead Cowboy
0:42
They said Dreadhead don’t come on the eastside of #chicago | Dreadhead Cowboy
67.9K views8 months ago
FacebookDreadhead Cowboy
1:24
Poor horse this dude got this horse outside in Chicago city st past midnight and he got drug dealers riding it and got guns and weed following out his pockets smh somebody tag the authority 😔 | Dreadhead Cowboy
16.9K views9 months ago
FacebookDreadhead Cowboy
0:35
They say DREADHEAD COWBOY gone have the key to the city soon #chicago #Illinois | Dreadhead Cowboy
7.8K views5 months ago
FacebookDreadhead Cowboy
1:32
Bye for now #rockfordillinois I enjoyed myself now I’m on my way back to #chicago | Dreadhead Cowboy
9.6K views6 months ago
FacebookDreadhead Cowboy
0:46
Crazy scene as horse-riding protester shuts down Chicago highway as police give chase
1 viewsSep 22, 2020
DailymotionNewsflare
1:08
Dreadhead Cowboy on Instagram: "my #1favorite moments in 2025"
2.5K views4 months ago
Instagramdreadheadcowboy_
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Working with “CHICAGO” 🐎 | Dreadhead Cowboy
11.3K views6 months ago
FacebookDreadhead Cowboy
0:13
Big shoutout to Chicago police for always showing me love wen they see me | Dreadhead Cowboy
184.9K views11 months ago
FacebookDreadhead Cowboy
0:13
They say only in Chicago | Dreadhead Cowboy
142.9K views11 months ago
FacebookDreadhead Cowboy
2:00
Chicago's Dreadhead Cowboy rides horse on Dan Ryan Expressway, faces 3 charges from ISP
Sep 21, 2020
ABC7 ChicagoLeah Hope,Rob Elgas,ABC7 Chicago Digital T…
Dread Head Cowboy pleads guilty to animal cruelty for galloping horse on Dan Ryan
Jan 21, 2022
suntimes.com
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Working with Chicago getting him ready for 2026 | Dreadhead Cowboy
5.8K views7 months ago
FacebookDreadhead Cowboy
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Short videos

1:56
1st day working with “CHICAGO” 🐎 | Dreadhead Cowboy
4.9K views6 months ago
FacebookDreadhead Cowboy
0:26
Working with “CHICAGO” 🐎 | Dreadhead Cowboy
11.3K views6 months ago
FacebookDreadhead Cowboy
0:13
They say only in Chicago | Dreadhead Cowboy
142.9K views11 months ago
FacebookDreadhead Cowboy
0:15
Chicago im out here | chicago
4.6M viewsApr 12, 2023
TikTokdreadhead_x
1:08
Dreadhead Cowboy on Instagram: "my #1favorite moments in 2025"
2.5K views4 months ago
Instagramdreadheadcowboy_
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#imglokk #lightskinned #dreadhead #chicago
13 views2 months ago
YouTubeGlokk
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They say DREADHEAD COWBOY don’t come to #calumetpark #Illinois
194 views6 months ago
FacebookDreadhead Cowboy
0:08
#chi #chicago #viral #dreadhead #makemefamous
436 views3 months ago
TikTokybnamed.zj
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Dreadhead Cowboy on Instagram: "Flipping off a big horse ain’t the same as flipping
2.2K views3 months ago
Instagramdreadheadcowboy_
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#lightskin #dreadhead #chicago #xyzbca | Dread Head
652 views2 months ago
TikTokwheremyblackqueen
0:08
🫩 #foryou #dreadheads #chicago #blowthisup #relateable | Dread Heads
817 views3 months ago
TikTokkyrasecretaccountt
3:55
Man… I’m pissed off right now. 💔🔥 Did y’all hear about that family that got KICKED OUT of the
7.5K views5 months ago
FacebookDreadhead Cowboy
0:07
5 day on training “DREAM” on a leash 🐐 | Dreadhead Cowboy
8.5K views11 months ago
FacebookDreadhead Cowboy
0:47
It might not be a big deal to yall but it’s all about creating memories for me
3K views9 months ago
FacebookDreadhead Cowboy
0:24
Dreadhead Cowboy on Instagram: "They say DREADHEAD COWBOY
80K views4 months ago
Instagramdreadheadcowboy_
0:08
Prom 2025 it’s the turn up for me | Dreadhead Cowboy
17.3K views11 months ago
FacebookDreadhead Cowboy
0:15
Day 1 of me teaching my goat how to ride 🐎 | Dreadhead Cowboy
2.3K views11 months ago
FacebookDreadhead Cowboy
0:15
At Ya Headdd😤#chicago #dreadhead #chiefkeef
655 views6 months ago
TikToktae_marlonfrmdao
0:16
They say wen people getting money they act different Prom 2025 | Dreadhead Cowboy
94.9K views11 months ago
FacebookDreadhead Cowboy
1:04
No grooming during the winter and this is what happen | Dreadhead Cowboy
37.3K viewsMay 16, 2025
FacebookDreadhead Cowboy
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