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In the new Suicide Squad pictures, Deadshot (Will Smith) is not wearing his mask.
Whether in comics or animated TV shows, I've never seen Deadshot without his mask.
Does Deadshot remove his mask often / ever in canon?
As far as I know Floyd Lawton AKA Deadshot has never had a problem taking off his mask in the comics.
Or in the cartoons.(Justice League Unlimited: Task Force X)
Required, but never shown