There's this recent video showing a little of what the Pharo Smalltalk environment is like:
https://www.youtube.com/watch?v=HOuZyOKa91o
The video was made by a Ruby programmer, rather than an experience Smalltalker, so it's more a newbie showing you cool things he's discovered, rather than an expert showing the power of the system.
On the other hand, there's this one:
https://www.youtube.com/watch?v=o4-YnLpLgtk
That one is an expert, Kalman Reti, showing some of what it's like to work with a Symbolics Lisp Machine. (It's not a real Lisp machine; they're all at least thirty years old now; this is an emulator running the old Symbolics OS on Linux).
Go to YouTube and search for Rainer Joswig and you'll find a few video demos of Lisp Machines and MCL and so forth.
Finally, here are a few images from about eighteen years ago, also from Rainer. They show various views of the Macintosh Common Lisp and SK8 environments. It's not an experienced user showing you around, but at least you can get some idea what the environments looked like:
http://www.lemonodor.com/archives/000028.html