The record for double entendres?

This is NSFW.

Guinness World Records doesn't monitor this, but I nominate The Greaseman's raunchy comments overdubbed onto Milton Brown's Somebody's Been Using That Thing as #1 in double entendres:

https://www.youtube.com/watch?v=_lQi7o0xXxE

If you enjoy the music (I certainly do), here's the original sans overdubbing:

https://www.youtube.com/watch?v=HplpbDRu0x4

If you are fond of the old timey you may wanna check out Charlie Poole and his North Carolina Ramblers. 

Listen to the song "Candy Licker" by Marvin Sease...its full of raunch, double entendres and many other things left to the imagination!