What does this remind me of...
Perhaps every Conan O'Brien skit ever? Very similar to Brian Stack's comedy (Hannigan the Traveling Salesman, Artie Stack, etc.), but still pretty funny. The danger I see, personally, is that after 12 years of Conan the old-timey gags are worn out. Unless done absolutely *flawlessly* (and sometimes even then) the jokes are just tired. Then again, other people still eat that stuff up, so there's certainly a market of people who sincerely enjoy it.