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Aww man I wish I would have snapped a screenshot of it now. The funniest thing that happened to me was that it thought that a desk fan sitting on my desk at work was my 10 month old son.
 
this one is funny for a couple of reasons, imo
 

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Face victories

I tagged my 5 year old niece's name, and iPhoto correctly identified her infant photos as her, even better than I could have...
 
face detection is .... OK

It's not perfect, but I wasn't expecting it to be. Still, was a bit surprised at the following result...
 

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My favorite

No screenshot, but when it asked if a camel hump was my sister I about fell off the chair laughing.
 
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