I was a fan of Jay's Tonight Show, but I'll admit that it's harder to come 
up with key memorable moments for Jay than it is for Dave. One reason is 
that Jay didn't do annual self-congratulatory highlight shows - he hated 
that format, and only did it once, for his tenth anniversary. Clips from 
that show, and from the highlight reel on Kevin Eubanks' final show (with 
the "masturbating in a tree" bit), are about all you can go to for 
highlights. Usually with Jay's Tonight Show, especially in those 
pre-YouTube days, you have to rely on your memory because your first time 
seeing a skit/interview was your only time seeing it.
 
(Also, I don't think Jay's staff was nearly as good at cataloging clips as 
Dave's was. Even some of Jay's landmark clips, like Steve Allen and Jack 
Paar's 1994 appearances, were never repeated - not when Allen and Paar 
died, not even when Jay discussed them with Betty White during the show's 
final week. I don't think they considered that stuff important, 
unfortunately.)
 
But off the top of my head, I'll mention his Beyondo skits; 
Jaywalking/Battle of the Jaywalk All-Stars; his interview skits with Jack 
Riley, Fred Willard and Gilbert Gottfried; Lawanda Page as Aunt Esther 
whacking "Johnny Cochran" with her handbag ("You lyin' Johnny Cochran - I 
want my palimony, and I want it now!"); an interview with Carla Gugino 
where Jay lost track of the conversation because he was staring at her 
cleavage ("You know what, I'm still a guy"); and Michael Richards pulling 
Jay's desk apart. I'm sure I could think of a lot more if I tried.
 

On Monday, June 1, 2015 at 5:52:05 AM UTC-4, JW wrote:

> While reading a recent Mark Evanier blog entry about Dave Letterman (
> http://www.newsfromme.com/2015/05/30/todays-video-link-1976/), I found 
> myself with a question that I'll ask this group. What were the 
> great/memorable moments during Leno's run on The Tonight Show? (Yes, I'm 
> asking seriously.)
>
> Beyond "What the hell were you thinking?", which is lessened by the 
> generic apology that was Grant's answer, I'm having a hard time coming up 
> with anything.
>

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