This study reported on the pragmatics of irony in humor in Vice Ganda's conversational jokes as an emerging drift in Philippine witticism. We analyzed a 52-token corpus of conversational witticisms (CWs) of the subject across the forms of media where he delivered this kind of witty and humorous utterances. Through the analyses made, We were able to find out that in using irony as a strategy to achieve a humorous CW, other or all of the Gricean Maxims could be violated without affecting the ironic effect of a humorous CW. The results and findings of this study could be utilized to identify some elements that are present in today's Philippine humor in conversations. Also, this study could be used as a baseline for studying more features of the least studied field in Philippine linguistics--Humor.