Jay Leno is the Everyman. Remarkable, considering how fantastically wealthy he has become. Despite his wealth and fame, Leno has managed to retain the persona of the wry, smirking Everyman.
I have to admit, when I was a teenager I preferred Letterman's more biting sarcasm. But as I grew into adulthood I found I preferred Leno's more gentle and good-natured humor. I think Letterman also became a good bit meaner, and at times nasty, over the years, but it's hard to tell.
For whatever reason, I feel Leno's humor has held up better over the years. He's clever and witty without being mean and dirty. Leno clearly likes people. He likes Americans, with all of our faults and all of our silly insecurities. Leno is always laughing with us and not at us.
Leno is not a cutting edge comedian. He's not leveling withering sarcasm at America. Rather, he's a comfortable presence and delivers, day-in and day-out, good-natured ribbing of America and our imperfections. There's always a caring twinkle in Leno's eye,and that's why he's been welcome in America's family rooms for so long.