That image is, of course, from Crispin Glover's legendary appearance on the David Letterman show in 1987. He showed up in a wig, striped pants, and shoes with giant heels acting like he was on drugs (on later Letterman appearances he claims to have been in character... or that it was not even him). It's a little hard to describe what happens, but the climactic moment is when Glover attempts to show off his kicking prowess. Check out an old article on Waxy.org here for more details. This bizarre incident repeatedly crops up in interviews with Crispin Glover, though I had never actually seen the clip until today. There's a pretty good video of the interview here (link at bottom of page). Strange stuff.
Anyway, some Crispin Glover covers!
Ben [originally by Michael Jackson]
This song has a strange story in its own right. The original song was MJ's first hit as a solo artist from the film Ben, which was a sequel to the 1971 movie Willard. Ben, if you were unaware, is one of Willard's pet rats who eventually rebels and becomes the leader of an army of killer rats. It's the only song I know of that is an ode to a rat. Okie dokie, then. In 2003, Crispin Glover starred in a remake of Willard and covered this tune for the soundtrack.
These Boots are Made for Walking [originally Nancy Sinatra]
This is the craziest, but funniest cover I've ever heard of this song from Crispin 'Hellion' Glover's album "Big Problem Does Not Equal the Solution. The Solution = Let It Be." His delirious vocals are somehow more sincere and palatable than Jessica Simpson's version... well, it makes me laugh anyhow.
[EDIT: I forgot to mention that Mr. Glover will be playing the role of Grendel in the currently-in-production Neil Gaiman/Roger Avary-penned Beowulf, directed by Robert Zemeckis. Angelina Jolie will play his mother (no joke).]