Not super obscure, and somewhat over shadowed by Rescue Me later-on, Dennis Leary's short-lived "The Job" (2001) was another funny comedy series from a stand-up comedian, and the "likable a55h0le" premise is similar too.
The Job is one of my all time favorite shows. Any fan of Dennis Leary, or has ever had a job, should definitely check it out. The Job is similar to The Office (both of em) but it was made like a decade earlier.
And I'm enjoying Legit as well. But had to chime in on your outstanding recommendation.