Well, this was back in '85, while Howard was still with WNBC and well before he was a household name. It was his first big remote extravaganza, a week-long series of shows from a swanky Hollywood hotel. A song parody contest was held to come up with ten guests for the trip. I wrote a parody of Howard's punkish theme song and it was good enough to win me a spot out of the thousands submitted. In fact, he used it to open his show every day. (I am currently receiving no residuals, though.)
It was a great trip filled with sun and fun and booze. Besides the five shows done poolside, during which the contest winners participated frequently (I sang a couple of my songs and did a commercial for the Beanstalk Restaurant, where I had dined a few times), we got to hang out with the Stern staff. I am remembering an especially rowdy party one night hosted by "Fat Al" Rosenberg and Gary Dell'Abate (details of which I am reserving for my memoirs). Howard pretty much kept to himself when not on the air, but Robin Quivers hung out a few times. I found her exactly as she is on the air: funny, brilliant and magnetic. We also got to meet and chat with some of the show's guests, which included Monty Hall, Eddie Haskell and Grandpa Munster.
I suppose the highlight of the trip for me was getting the hook from Howard while I was doing one of my tunes, which he declared sounded "like Joni Mitchell." Fred played a "howling dog" sound effect during it, and Robin advised me to not quit my day job. While my father later told me he'd heard it all and wanted to punch Howard "right in his big mouth," I assured him it was not only a funny bit but a personal honor. I don't think he ever agreed.
The week went all too fast but it was a blast and the occasion of many great memories. Thanks for asking, Frank.
P.S. As I have taken the day off and have some free time, I have included a few photos of the trip:

Here's me just before I got the hook.

I had to get out of the hot tub to take this shot. One of the few times Howard socialized.

From the left: "Fat Al," Fred Norris, myself, Ken Osmond, my pal Jim Clune.

Of course, it wasn't all hard work.