Great guy; great talent.
I worked with him for 6 years. For 4 we were on "sister" stations and talked in the halls, and for 2, I followed him on the air.
Jack was a creative machine. He was constantly coming up with ideas and verbalizing them. Many of the best weren't "air acceptable" but were damned entertaining. Though I'd never seen the show to that point, I did an accent that always made Jack crack up. He told me it sounded like "that old perv on Family Guy". After I checked out "Herbert", I had to agree with him. He and I would hold entire conversations using the voice of Herbert and try to "outgross" each other. Neither man ever blinked, but one might crack up first.
Jack used to do spots sometimes that'd feature like 3 different voices, and he would do them all. When one of these ads would air, I would play a little game called "which Jack Boston am I" and imitate the voices ("I'm the intimate Jack Boston..I'm the angry Jack Boston, I'm the redneck Jack Boston", etc.). He got a kick out of it.
Though he was a great air talent, he was a RARE and EXCEPTIONAL production talent. His stuff was of the first order, even down to the music he used to set the mood. No stone unturned. There are great voiceover people and there are great production people and rarely do the two meet, but Jack was F-in world class in both areas. Clients rightfully loved his ass. He was also great as an M.C., he could really work the room. I always hated to have to be the "next guy at the remote" after him, because I could never put on the floor show that was Jack Boston.
He loved his family and bragged on them often. I can't tell you how many football videos of his sons he made me watch.
Many do not know that Jack worked at WLS, Chicago in the 80's, and that he spent time as an actor in NY as well. Linda Fiorentino (Men In Black), told him that she thought he was hot (he wasn't single at the time). Never a negative to have a hot actress think you, too, are hot. Jack was a charismatic, bigger than life character. All the comments on the boards, websites, publications, plus many on air tributes more than prove the point that Jack wasn't "just another guy".