The smug-yet-wisecracking boss that employees both fear and love? Think: Jimmy James from NewsRadio or Dr. Cox on Scrubs? (Or any character John C. McGinley seems to play.)
You can scroll down through the categories that Cox has on TV Tropes and see if any meet what you're looking for.
https://tvtropes.org/pmwiki/pmwiki.php/Characters/ScrubsMainCharacters
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