Watch This: David Letterman at the Oscars

David Letterman

After an impressive 33 years, late night talk show host David Letterman will be retiring from his job as the host of The Late Show. For many, it is the end of an era that was full of anarchy and very odd comedy choices. Unlike his competition, specifically that of Jay Leno (The Tonight Show), he was influential in making pranks and lists into an art form for hilarity. With all of this in mind, it is interesting to note that his Academy Awards hosting gig has gone down as one of the worst, yet is it considering the countless names that have come since (Ellen Degeneres, James Franco, etc.)? Along with celebrating the 20th anniversary of that frightful gig this year, it is as good of a time as any to revisit it as we lose one of the most inimitable and ornery talk show hosts in American history.

The premise was simple. Due to an unqualified success with former The Tonight Show host Johnny Carson proving to be among the best Academy Awards host, they would allow Letterman to host. He is after all the man who once did an entire show in which the camera consistently tilted the image. He was an auteur of creative programming. When 1994's host Whoopi Goldberg and Billy Crystal refused, they gave the gig to Letterman. Not only was it because of Carson's reputation, but because producer Gil Cates claimed that Letterman was punctual. Also, due to international tragedies, the theme of the night was "Comedy at the movies." It was a match made in heaven, or so things would seem.

Along with Chevy Chase's infamous "Hello Hollywood phones," Letterman's first words as host have gone down as one of the strangest experiences in the ceremony's history. It is a moment that has been lampooned to death and highlights a particular ongoing feud with Oprah Winfrey. Ladies and gentlemen, the Oprah/Uma moment:

It was a moment that doesn't even clock in at a minute. The choice to introduce Winfrey to Oscar nominee of the night Uma Thurman (Best Supporting Actress - Pulp Fiction) is a gag that is of very few words and has no deeper contexts. Even the additional reference to Keanu Reeves has been forgotten. The bigger question is why this gag has been remembered throughout history and even 20 years later. At most, it is... odd in ways that Letterman mastered on his show. If you didn't get it, there's a slight chance that it could be funny that way.

Yet there were some more astounding things to go on during that Academy Awards ceremony. He managed to incorporate a lot of The Late Show routines into the actual show. The most noteworthy was that of his Dumb Pet Tricks routine, featuring a cameo from nominee and winner of the night Tom Hanks (Best Actor - Forrest Gump), who helped him set up the stage.

The gag was minimalist and served more as a throwaway gag. The whole point of this Dumb Pet Tricks was that the dog chased his tail when the audience applauded. Composer Bill Conti provided music with the orchestra. It came and went with Hanks getting razzed by Letterman claiming that it was "Almost as good as winning something." It was a funny statement considering what would happen later. While it wouldn't be the last dog at the Oscars (Uggie from The Artist in 2012), it was a nonsensical gag that had very little to do with anything of the evening. So far, Letterman was doing his shtick to perfection.

Then of course, there's the thing that couldn't have been avoided. Letterman needed to do a Top 10 for the Oscars. This also included a gag reel from his film Cabin Boy in which various celebrities are told to read the line "Would you like to buy a monkey?" 

There's a lot to unravel about this video. The most noteworthy is that in a night referencing "Comedy at the Movies," it was done through the art of repetition and celebrities reading the simple sentence in absurd tones. Depending on how much you can enjoy overacting, it was splendid. However, the very idea that the film of choice was Cabin Boy is rather comical considering how little of a legacy that film actually has. If anything, it was also rather subversive considering that the Oscars embody prestige and even now, 20 years later, haven't come around to acknowledging comedies of Cabin Boy's ilk. Also, there was a nice jab at the Oscars during the Top 10 segment, in which he joked about them not nominating Hoop Dreams.

While there's a lot more show, it is difficult to track down nowadays. If you wish to watch the acceptance speeches, you can consult The Oscars' Youtube page about that. However, the legacy is well known and the Uma/Oprah routine has stained his career. With many considering the rest of his show to be a disaster, it makes sense why he hasn't come back and only jokes about the ceremony with guests on The Late Show. While there are very few who give him respect (The Buffalo News gave him a good review), but it was mostly one that people considered to be the worst. Still, it feels like the form of anti-comedy that he has always been known for, almost pranking the audience with awkward jokes, random routines, and even a few adaptations of The Late Show's most beloved gigs. 

With his departure tonight from The Late Show, it is interesting to look back at one of the strangest nights of Academy Awards history. While there have been worse since (Ellen Degeneres in 2014), he remains an outlier for doing things his way. As the show embraced spectacle, he decided to roll out carpets for dogs chasing their tail. In a sense, he was amused by the little things. It is always how he was. For a man with a very odd 33+ year career that has resulted in countless memorable moments, it is sad to see him go. He embodies the last of an old way of thinking in an era before viral videos and online content replaced putting on a show in the moment without worrying about constant interaction. Maybe he wasn't the best. Maybe the Uma/Oprah gag will be his biggest mark. Who knows. However, it's amazing to see just how odd he was and how confused he likely made audiences as they waited for the Best Picture to go to Forrest Gump. In a way, he was the ultimate box of chocolates. Nobody knew what they were going to get out of him.