I think so but only when you humanise the brand.  Logos don't have humour.  People do.  

When businesses are comfortable enough to put their employees in front of their logo, magic happens.  Networks build.  Connections thrive.  Relationships deepen.  All of this goes towards humanising the brand.

Obviously not all humour travels across borders but in most cases, "don't take yourself too seriously" humour can work to build empathy and trust with audiences.  

I like the idea of businesses sharing their light-hearted side.