| 2019-02-26 | THE GREAT ESCAPE in Prison Boss PSVR #8 (PlayStation VR Gameplay) | 30:22 | 9,067 | Let's Play | Prison Boss VR
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| 2019-01-18 | DOING THE BOTTLE FLIP CHALLENGE IN JAIL! | Prison Boss #7 PSVR Gameplay | 17:30 | 6,086 | Review | Prison Boss VR
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| 2019-01-15 | BREAKING OUT OF JAIL! | Prison Boss #6 PSVR Gameplay | 18:23 | 7,608 | Review | Prison Boss VR
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| 2019-01-05 | SNEAKING IN THE ALCOHOL! | Prison Boss #5 PSVR Gameplay | 31:15 | 22,360 | Review | Prison Boss VR
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| 2019-01-03 | I BECOME THE RICHEST PRISONER EVER! | Prison Boss #4 PSVR Gameplay | 25:54 | 8,858 | Review | Prison Boss VR
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| 2018-12-30 | THE LEGEND OF THE GOLDEN BOBBY! | Prison Boss #3 PSVR Gameplay | 22:10 | 9,748 | Review | Prison Boss VR
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| 2018-12-14 | EARNING A FORTUNE IN PRISON! | Prison Boss #2 PSVR Gameplay | 23:21 | 13,671 | Review | Prison Boss VR
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| 2018-12-11 | THE RETURN OF THE PRISON BOSS! | Prison Boss PSVR Gameplay | 19:38 | 17,545 | Review | Prison Boss VR
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| 2018-06-13 | VR PRISON SIMULATOR | CrossSide The Prison VR gameplay - HTC Vive Gameplay | 11:32 | 4,020 | | Prison Boss VR
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| 2018-05-02 | AFTER PRISON BOSS: HOW TO BECOME A KNIGHT IN VR! | Jousting Time - HTC Vive Pro Gameplay | 19:11 | 19,484 | Guide | Prison Boss VR
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| 2017-09-24 | PRISON BOSS FAREWELL STREAM! | VR Sundays with Rowdy #14 | 1:50:18 | 115,603 | | Prison Boss VR
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| 2017-09-20 | ESCAPING OUT OF THE LAST PRISON! | Prison Boss VR #10 - HTC Vive Gameplay | 28:32 | 570,226 | | Prison Boss VR
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| 2017-09-15 | I GOT CAUGHT! | Prison Boss VR #9 - HTC Vive Gameplay | 44:39 | 1,028,908 | | Prison Boss VR
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| 2017-09-08 | THEY THREW ME IN THE STAR WARS PRISON! | Prison Boss VR #8 - HTC Vive Gameplay | 35:20 | 462,322 | | Prison Boss VR
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| 2017-09-03 | PRISON BOSS VR #7! | VR Sundays with Rowdy #11 | 1:53:07 | 1,257,902 | | Prison Boss VR
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| 2017-09-02 | BREAKING OUT OF THE SECOND PRISON! | Prison Boss VR #6 - HTC Vive Gameplay | 28:51 | 7,042,859 | | Prison Boss VR
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| 2017-08-29 | GETTING RICH IN VR PRISON! | Prison Boss VR #5 - HTC Vive Gameplay | 35:15 | 452,660 | | Prison Boss VR
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| 2017-08-27 | MAKING HOOKAH IN THE VR PRISON! | Prison Boss VR #4 - HTC Vive Gameplay | 31:42 | 360,878 | | Prison Boss VR
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| 2017-08-26 | BREAKING OUT OF THE VR PRISON! | Prison Boss VR #3 - HTC Vive Gameplay | 25:51 | 249,430 | | Prison Boss VR
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| 2017-08-23 | PRISON BREAK IN VR! | Prison Boss VR #2 - HTC Vive Gameplay | 30:38 | 350,087 | | Prison Boss VR
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| 2017-08-21 | THE ESCAPISTS IN VR! | Prison Boss VR - HTC Vive Gameplay | 28:12 | 430,221 | | Prison Boss VR
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