This last Friday, Jay Leno hosted his last The Tonight Show episode before his move to a 10pm Monday-Friday primetime variety show in the Fall.  I watched the show and realized that it was the first time in several years that I had watched one of his shows all the way through, although I had seen an occasional segment or two when someone of interest was a guest on the show.

I have really never been a fan of Leno’s version of The Tonight Show, which came as both a surprise and a disappointment to me.  I pretty regularly watched the show when he was the permanent guest host for Johnny Carson and usually enjoyed it quite a bit.  In fact, I had felt that Carson had kind of started to phone in the show during his last few years and I frequently found Leno’s shows to be more engaging.  Leno had also been a very frequent guest on Late Night With David Letterman and was consistently very funny during those shows.

I was going to college in Milwaukee during the late 1980s when Leno was most frequently guest-hosting for Carson.  Twice during that time, Leno brought his touring stand-up comedy concert to town and I went to see him both times.  I can’t really think of many, if any, other shows that have made me laugh harder and more consistently than those two shows.  As a concert stand-up comic, Leno was (probably still is) absolutely hilarious.  I resisted for quite a while buying a ticket for the second concert (which was about a year or so after the first), but my memory of how funny that first one had been eventually got the better of me.  The second time was just as funny and I recall being pretty stunned at how little repetition there was between the two shows.

With all that, I was surprised that I never could warm up at all to Leno’s version of “The Tonight Show”.  I watched the show quite a bit during its first year or so and have continued sampling it periodically over the years, but I have always found the show to be bland and generally not too funny.  I recall liking him much better when guest-hosting for Carson, so much of the problem may come from his own shaping of the show’s style and format.  While I found Leno to be both ingratiating and tremendously funny as a concert stand-up comedian, I generally found him fairly smarmy and even a bit irritating as a talk show host.

The interview segments that I’ve seen have been particularly weak, with Leno allowing way too much latitude for the guests to plug whatever project they are on to promote.  He didn’t seem to be very effective at providing support to guests that were less than comfortable with the format, either.  Last year, I watched his interview with Harrison Ford when he was on the show to promote the new Indiana Jones film.  Ford is notoriously uncomfortable in interviews and has a real tendency to become almost painfully silly unless the interviewer works hard to steer the conversation.  His interview with Leno was borderline embarrassing and a rather stark contrast compared to the segment Ford did with David Letterman the following week.

While I’m sure that Friday night’s final show wasn’t really a representative sample, I still didn’t really see much improvement.  Leno’s monologue wasn’t bad (stand-up is obviously his true calling), although the material seemed a bit thin and Leno kind of over-sold it.  The only interview segment was with Conan O’Brien, the new host of The Tonight Show.  Not surprisingly, it was really more of a passing of the baton than a real interview.  The musical guest was James Taylor, who was apparently a Leno favorite, but is not that dynamic a performer.

The result was fairly boring, leading me to think that he really needed to bring on very strong closing guests that would have left more of a lasting impression to help lead up to his new show in the fall.  I could see a potential argument that this wasn’t really a true “farewell” show since Leno is really just moving to an earlier timeslot, but it still seems that this show was sure to get a bit more of an audience (the reports are that the ratings for Friday were double the average for the show) and it would have helped for this show to leave the viewers wanting more.  I think back to David Letterman’s final NBC show where the guests were Tom Hanks and Bruce Springsteen (making his first appearance on the show), which felt much more like an event.

Leno closed the show with a fairly sweet segment at the end where he brought out all the children that had been born to Tonight Show staff members during his tenure as host.  This was a nice ending, although naturally it would have had a lot more meaning for the staff than for the audience.  The segment also seemed a tad rushed, without any time for Leno to directly interact with any of the kids.  It also struck me as a little off that the very last part of the show was something that was directed more towards the staff and crew than the show’s audience.  My sense is that this might have been a more effective segment for the show’s midpoint, preferably with a bit more actual participation by the kids, and that he would have been better off ending the show with a “see you later” speech that was a little more squarely directed at the studio and home audiences.

Other than the monologue, there was only one major comedy segment during Friday night’s show, which was a highlights reel from Leno’s recurring “Jaywalking” segment.  I had heard references to this as Leno’s most popular comedy bit, but I don’t think I had ever seen one of these segments before.  It is a “man-on-the-street” segment where Leno would go up to people and ask them fairly simple history or current events questions.  The bit would then be edited together from incorrect responses, sometimes with Leno kind of trying to bait the respondents into either a correction or digging themselves deeper.

What struck me was that the segment not was pretty unfunny to me, but it was also surprisingly mean spirited.  It definitely felt like Leno was asking the audience to laugh at the people and not with them.  Despite the flaws with his show, I had always generally found Leno’s comedy to be pretty gentle, remaining fairly good natured even when going after political or celebrity targets.  Certainly, he has long had a reputation for being a nice guy, particularly compared to David Letterman’s more acerbic approach.  Even in the live concert performances I attended, Leno worked very clean (no profanity or significant scatological material) and his comedy was much more observational than confrontational.  The “Jaywalking” bit seemed pretty out of character.

I should acknowledge that I have been a long time David Letterman fan, extending back to before I even had heard of Jay Leno.  I initially discovered Letterman’s NBC show fairly early in its run and would watch it whenever my Junior High School schedule would allow.  Once we got a VCR (during my sophomore year of high school), the show became a usual part of my after-school ritual.  Throughout college, I watched the show as it aired most nights, helped by the fact that it came on 11:30 in Milwaukee.  I don’t watch his show nearly as often today, but we do still have our DVR set to record it each night and occasionally pick and choose an episode to watch (often based on who the guests were) when time allows.

While I was never overly impressed with Leno’s version of the show, I did at least tune it in periodically before Letterman moved his show to the same timeslot over on CBS.  If it weren’t competing with a show that I prefer by quite a bit, I suppose I might have continued to tune in a bit more.  While I don’t think that Letterman is nearly as daring as he was during his early days and his show has probably fallen into way too much of a routine, I do also think he is the top master of this form of program at this time, having now attained a skill level that rivals Carson.

Despite my admiration for Letterman’s skills, I’ve never really been in agreement with those (possibly including Letterman himself) that felt that NBC made a mistake by giving the Tonight Show job to Leno instead.  I think Letterman would likely have been overly constrained by the legacy of The Tonight Show, particularly by the likelihood that he would have succumbed to the pressure to do the show from Southern California instead of New York.  I think he has been better served by creating his own franchise without being bound to maintain someone else’s tradition or do the show from a venue that isn’t as good a fit to his style.

I also have to acknowledge that the choice of Leno over Letterman was almost certainly the best thing for NBC.  Unquestionably, there is a huge amount of subjectivity to one’s reaction to comedy and entertainment in general and there is a lot of indication that many disagree with my subjective opinion of Leno’s Tonight Show.  The show has maintained pretty consistently good ratings during Leno’s tenure (after a bumpy first couple years) and it has usually had more viewers than Letterman’s show by a pretty wide margin.  I honestly am not really sure why, but Leno’s show clearly has had quite a bit of mainstream appeal.

Despite being generally unimpressed with the show over the years, I still have very fond memories of those live shows that I saw and I guess I do still have something of a soft spot for Leno.  That is why I wanted to watch his last show and I suspect I will at least give his new show a chance this fall.  I’ve heard that it may shift more towards a comedy/variety format rather than the usual late night talk show approach, so maybe I’ll find this one to be a better fit for his talents.  I actually hope that is the case.