I think WXRT 93,1 FM (adult alternative/deep cuts) in Chicago has had the same DJs since about 1980! I kid you not!
There was an FM station that used to have comedian Bill Leff on their morning show. He was an odd fit but I really got a kick out of his rather off-beat sense of humor. Leff later ended up as a co-host on the Roe Conn Show over on 890 AM but his contract wasn't renewed and his last show was back in May 09. He was on WGN 720 for one of their Saturday shows for awhile but he ended up leaving WGN of his own accord.
I'd like to hear him either get his own show or end up back on Roe Conn. He had some great throw-away lines. And honestly his humor is largely about delivery. He can take some really cornball hokey comedy and make it much funnier just with his delivery of the humor. I miss that.
Back to Sirott though. He is now one of the evening news anchors on WGN's 9 o'clock news. NBC had him but totally blew it. He was on contract and everything. They tried to renogotiate his contract and he ended up walking... their loss. Bob was a great fit on NBC 5.