He got his start as the Weekend Update anchor on Saturday Night Live from 1985note to 1991, making him the first long-running Weekend Update anchornote and the first SNL cast member to stay on the show for longer than five years. Prior to that, most cast members either were dropped after one or two years or stayed on until their fourth or fifth year (often leaving to star in feature films or other television shows). Miller opened the door for other long-running cast members like Darrell Hammond, Phil Hartman, Tim Meadows, Kenan Thompson, Fred Armisen, Bill Hader, and fellow Weekend Update anchors Tina Fey and Seth Meyers (the only other Weekend Update anchors to stay on past the fifth-year mark).
Though Miller acknowledged that he wasn't good at acting in sketches and felt at home as a Weekend Update anchor (as it was an opportunity for him to do his stand-up), there were rare times where he was in sketches. His recurring characters were Koko, a forest sprite from the short-lived recurring sketch "Miss Connie's Fable Nook" and Steve, a sarcastic observational stand-up comic (seen on a season 11 sketch on the episode hosted by Jay Leno and a season 13 sketch on the episode hosted by Tom Hanks). His celebrity impressions include Nathaniel Crosby (Bing Crosby's son), Senator Gary Hart, and George Harrison from The Beatles.
After his stint on SNL, Miller hosted a short-lived late night talk show The Dennis Miller Show. After the show's cancellation but before it went off-air, Miller began indulging in long-winded and humorous rants about social and political issues. The rants caused such a stir that he parlayed them into a successful HBO talk show Dennis Miller Live, which combined a celebrity interview and a Weekend Update-like "news" segment with a humorous rant from Miller about a specific topic each week. The show ran from 1994-2002. During this time, he made a famous but abortive attempt at color commentating on Monday Night Football from 2000 to 2001, where his trademark obscure references were poorly received by football fans.
While Miller's politics have never been confined strictly to one side of the political spectrum, his commentary began to shift noticeably to the right after the attacks of September 11, causing an upheaval in his fan base. He is currently a regular contributor on the Fox News channel. Since 2007 he's also hosted his own radio show called The Dennis Miller Show.
Tropes associated with Dennis Miller include:
- Catch-Phrase: On Weekend Update he would begin with, "Good evening, and what can I tell you?" and end with "Guess what, folks? That's the news, and I am outta here." On Dennis Miller Live his rants would begin with "Now, I don't want to get off on a rant here, but..." and end with "Of course, that's just my opinion, I could be wrong."
- Rant Comedy: In the final episodes of The Dennis Miller Show, Miller began throwing out his scripts and simply using the platform to vent his beliefs on a wide range of topics. Audiences found the rants so entertaining that Miller made them a central focus of his next show, Dennis Miller Live, in which he performed a scripted rant Once per Episode. He even sold audiobooks of collections of his rants.
- Sesquipedalian Loquaciousness and Sophisticated as Hell: He mixes obscure references and big words with lots of slang, and when uncensored, cursing.
- Verbal Tic: Calling people "babe," something that no impression of him can dare omit.
- Viewers Are Geniuses: One of the main reasons why Miller is a polarizing comedian. Other shows have made fun of this, such as The Simpsons (season ten's "They Saved Lisa's Brain," where Comic Book Guy's "C:/DOS. C:/DOS/Run, Run/DOS/Run" shirt is only considered funny to one person out of a million (which is called "The Dennis Miller Ratio") and Family Guy (the Cold Open to "Peter Griffin: Husband, Father, Brother?" has Peter watching a monologue to Dennis Miller Live filled with obscure vocabulary and historical references — and Peter responding with "What the hell does 'rant' mean?")
- You Have to Have Jews: A humorous instance on Dennis Miller Live had Miller become bewildered by the presence of the word afikoman in his monologue, with no idea what the word means or how it's even pronounced. The reference was obviously added to the script as some Author Appeal by his Jewish writers without his knowledge.