To Want Him, Or To Be Him?

I've told the new guys at work to set their standards high, but not LW high. LW is a contract retread employed for thirty years, retired, and rehired until we can get some folks trained. One of LW's favorite phrases is "All the girls want me, all the guys want to BE me." I decided a while back to help build the legend in his mind, so I've been telling everyone about the inevitable disappointment of comparing one's self to him in any arena. "It's better," I say, "to just do the best you can, and know you've worked alongside the great one."
We have an excellent director who is openly gay, and I've never heard anyone joke about her before LW the other morning. He somberly shook his head and commented to nobody in particular, "It must be so confusing for her. She doesn't know whether to want me, or want to BE me."
Now, we all busted out laughing as he shook his head compassionately as he left the room, but I wondered later how a slightly different audience would have responded to the joke. Sexual preference is a protected category, and any reference could land you in HR discipline. I suspect that our manager would laugh along, because the joke is as much about LW, their relative positions in the organization, and his Fonzie-like self promotion than anything else, and we've heard the want-me-BE-me line for so long. But I know there are those who would perceive an attack, and relish the opportunity to escalate it.
LW can afford to take a risk for a laugh, and that adds to the humor. I may not want to BE him, but I wouldn't mind being in the employment position he occupies now. The cliche is "It's a great gig, if you can get it!"