Listen to old radio clips of the following--
- The Opie & Anthony Show
- The Phil Hendrie Show
Stern was exceptionally funny too...until somewhere around the turn of the millenia he simply stopped trying (or showing up to work that much...hoo-hoo)
OnA were especially on fire comedically when they added li'l Jimmy Norton and gave him '3rd chair,' (which was also done by Stern in the form of Jackie Martling and later Artie Fine, who are NOT as funny as li'l jimmy...hoo-hoo).
fill-ins on the 3rd chair (and/or guests) on the OnA show is a who's who of guys that can bring the funny. There were absolutely no constraints on the content and Greg Hughes created an environment where funny-guys could snap out of the usual "plug my next show at this radio station" and create priceless moments - almost always improvised. guys like Louis CK, Bill Burr, Anthony Jeselnik, Bob Levy and Patrice O'Neal. (RIP Patrice!)
Hendrie is bit more abstract than all of them -- you have to REALLY be thinking to get (and keep track of) how many levels and in how many ways his improv is hysterical. Best if you can get ahold of his KFI/Clear Channel recordings when he was doing syndicated drive-time and took live calls.