Personally, my version of Chris Messina is and always will be Danny Castellano from 'The Mindy Project.' In fact, that's how I first found out about him and now I'm a big fan. It's hard for me not to see him as a tough, confident man's-man, especially with that booming New York accent.
Well, don't use that deep voice to identify him if you're watching 'You've Got Mail.' In it he has a small role as a salesman at the Fox bookstore, but with being such a young lad at the time, you'd never recognize him by his voice. It's a tad high, to say the least, but he's still a knockout and the camera loves him. Age has only been kind to him, since 20 years later he's now considered one of the sexiest men in Hollywood.