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1.
A combination of two common football exercises. A serpentine, which requires those participating to jog across the football field using the horizontal yard lines as a path. Those doing a serpentine will start at one endzone and snake their way up five yards for each trip across the field until they've reached the other endzone.

A serpentine becomes a bearsnake when combined with bear crawls. Those unlucky enough to endure the pain of a single bearsnake will experience over 1,000 yards of bearcrawling back and forth across the field.

Because of the infamous difficulty of a bearsnake, the name has become a synonym for anyone who is stupid, retarded, socially awkward, or just plain derpy. If someone calls someone else a bearsnake it means they think so lowly of the person that their mere presence inspires the same pain as one would feel from doing bearsnakes.

Snakey (adj.) is used to describe people or things that possess attributes comparable to bearsnakes. It is not correct to say, "They are bearsnakey" or "They are like a bearsnake." One should exercise the use of this word in these situations.
Football Guy #1: Dude, I did 1/4 of a bearsnake yesterday!

Football Guy #2: Dude, no way! That shit's crazy difficult!

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Guy #1: I just heard from Tori that Jason prematurely ejaculates!

Guy#2: I'm not surprised. Jason is such a bearsnake.

Guy #1: Yeah, I guess he IS pretty snakey.
by TheAlmighty8 July 14, 2011
 
2.
A Bear-Snake is a bear (the animal of the Ursidae family) lacking both arms and both legs, creating a fuzzy snake-like creature. These limbs could be lost in a freak bear accident or the bear could have simply been born without them. This term can be taken literally, or a human could be referred to as a bear-snake if he/she is acting or saying things that perhaps a bear without limbs might do/say. Also, the word "bear" in the phrase could be replaced with another thing, if one were to encounter an object lacking the usual number of limbs. "Bear-Snake" is a versatile word, and is open to many different interpretations.

It is important to note that, while the meaning of this term changes based on context, the vocal inflections of the hyphenated words always remain as such: the word "bear" is spoken in the upper register, then the pitch decreases when the speaker says "snake". A veteran of the word "bear-snake" would increase pitch DURING the initial "bear", then decrease pitch whilst saying "snake" (creating a mountain-shaped pitch vs. time graph). The general idea is that the phrase is said in a sing-song fashion.
"Bear-Snake!"

"Hey Kaitlin, without legs, your bear keychain more closely resembles a bear-snake."
by Rogue Boinky September 02, 2008
 
3.
What's the only thing more scary than a bear or a snake? A spider. Bearsnake is a compound noun and generic term for a spider, formed by combining the names of 2 frightening creatures of the wild, the bear and the snake.

Bearsnake is typically used as an exclamation when a large scary spider is spotted in your immediate vicinity. There are some notable exceptions however. You will be ridiculed if you claim bearsnake on a small garden or house spider. However, for a particular leggy granddaddy-longleg spider, you are allowed to claim legbear. The ultimate and fortunately seldomly used version is wolfbear, which is reserved exclusively for the mighty tarantula. It is critical to never falsely claim wolfbear as this can render your friends in a state of panic and possible medical emergency.
Ahhhhh, bearsnake! At least it's not a wolfbear.
by UncleFreddy October 24, 2014