Does anyone know if Bossk (Pilot) works with Greedo?

This is how I imagine it in my head.
I shoot with Bossk. Get a crit. Before dealing damage, I cancel said crit for two hits (Bossks ability). Then Greedo makes the first hit dealt face up? (assuming the enemy is out of shields)

Yep, it's a legit combo.

Whether it's worth the price, the penalty, and the opportunity cost of losing a crew slot however, is very questionable.

Note that it only works on Bossk's first attack each round, so if you use Gunner Greedo won't trigger on the Gunner attack. Similarly, Greedo only triggers on the first incoming attack, so if your opponent strips your shields with one attack then shoots you again in the same round, Greedo doesn't trigger on the second.

Pair with k4 and calculation. Crits on crits on crits.

.I shoot with Bossk. Get a crit. Before dealing damage, I cancel said crit for two hits (Bossks ability). Then Greedo makes the first hit dealt face up? (assuming the enemy is out of shields)

Greedo doesn't make the first hit dealt a face-up card, he makes the first face down card be dealt face up instead. So even if your target takes the first hit on its shields Greedo can still trigger if any of the hit results deal a card.

In my experience, Greedo is not worth it.