Not sure it’s a good comparison. Comedy is a bit different animal than music. I’m not sure big stars like Rihanna, Taylor Swift etc would be able to become such big stars and maintain their fandom and deal with all the logistics of TV/radio promotion & deals, concerts, brand awareness and such alone without big studios doing that for them. I am not up to date on music but are there examples of big international pop stars who bootstrapped their superstar career without being promoted and pushed by one of the big three studios?
He was a writer for established media titans like Letterman and Conan, with other fairly-typical industry projects as well, with a TV show on a major cable network, before he really blew up outside of comedy insider circles, AFAIK.