This may seem like a lame question without much thought, and it really is, but did any (mainly Classical because we're all brainwashed into believing that this is the optimal stage of Latin, but other ages accepted,) authors use words that sound alike to make a joke about their relationship? If this is too broad, and there are far too many notable examples available, feel free to flag or vote to close it. In an example, please include a brief explanation of the context and like words.
The question can obviously never be answered completely, but the basic answer is of course yes. Puns are all around us, everywhere we go.
One of the examples I remember best, from class, is the rather grim wordplay in Apuleius, Met. VIII, 6 when a bride-to-be finds her future husband murdered:
invita remansit in vita
she remained, unwillingly, alive