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@ Steve, thanks for the comment! Not so much as a fascination with the cigar but thought it complimented the outfit and environment. Plus I told him he could just ditch it (I mainly just wanted to get the shot in #1 w/ smoke and be done with it) but he wanted to keep smoking it, so I worked with it.
@ Rodriguez, thanks as well! and as far as brand, I couldn't tell you. I only had 5$ in my pocket and bought the cheapest they had, haha... #7 may look a bit unnatural, but I thought it worked. I feel like any closer and it would have looked less relaxed and more forcefully posed.
@jojomon, thank you! I agree on the cigar complimenting the personality and style - that was my intent!
And I definitely agree with you on the cropping... that's something I'm still working on, I'm an aggressive cropper