10 Most Insane Prison Breaks Of All Time

8. Robert Dale Shepard's Dental Floss Escape

The Great Escape
By Stan Zurek (Own work) [GFDL (http://www.gnu.org/copyleft/fdl.html), CC-BY-SA-3.0 (http://creativecommons.org/licenses/by-sa/3.0/) or CC BY-SA 2.5-2.0-1.0 (https://creativecommons.org/licenses/by-sa/2.5-2.0-1.0)], via Wikimedia Commons

Dental floss can do wonders for your oral hygiene, but criminal Robert Dale Shepard found another use for it while he was holed up in a West Virginia jail in 1995.

Collecting packets of the cavity-fighting string from the prison commissary and other inmates, he braided seven reels of the stuff together and weaved it into a rope ladder spanning 18 feet.

As thick as telephone wire, the makeshift ladder was able to sustain Shepard's weight when he tied it to a cinder block and tossed it over a prison wall. He was free for 41 days before the authorities caught up with him and hauled him back to the slammer.

Shepard served 30 years behind bars, but several of those were for flossing his way to freedom. Many prisons banned dental floss in the wake of the incident.

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