Tim Rogers from You am I does this. He even acknowledges it (while demonstrating it) in one of his Temperance Union songs Dumb as being among his many faults. More recently, little-brother-country-indie-rocker Ben Kweller also strains to get higher than he strictly should in Sawdust Man.
But it sounds good when singers strain. We don't care when someone like Mariah Carey sings flawlessly high ; it's no big deal; we know they've got the skills, there isn't an obvious risk. When more workmanlike singers strain at the top of their voices it's like a special gift; it shows us their humanity and vulnerability. Their effort and passion is thrown into higher relief.
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One of my favourite singers, Jeff Tweedy (of Wilco) does this a lot. He did a live cover of 'Fake Plastic Trees' in which he bravely strained very high and got away with it.
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