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2nd Gen Ram Tech1994-2001 Rams: This section is for TECHNICAL discussions only, that involve the 1994 through 2001 Rams. For any non-tech discussions, please direct your attention to the "General discussion/NON-tech" sub sections.
Air in the system does a couple of things. Dirst, it allows moisture to remain in system whcih turns to acid, and it prevents the refrigerant from being filled to the correct level and has different compression proerties than the refrigerant.
You can recharge it, but it's a waste of time if you don't evac the air/moisture out. It'll contaminate the refrigerant, corrode components, and eventually cause leaks.