Most Difficult Shadow Pokémon to Catch?

[Sydney]

For those of you who've either played Colosseum or Gale of Darkness, you've must've caught quite a few Shadow Pokémon during your expedition. That being said, which capture was the most difficult for you? Did you manage to catch it, or was it too difficult, causing you to run out of Pokéballs? If you did catch it, how many times did it take and what type of Pokéball did you use? Discuss.

 

[Ventus]

Shadow flippin' Lugia. :/
I didn't get much witht he game - my friend had it way back when - but I tried to catch S.Lugia and it just didn't happen.

 

[Beeker]

Any of the legendaries really, since their catch rates are so low. But, to me, I'd say a really tough one to catch is Entei in colosseum. It's the first real challenging boss battle in that game, it has the low catch rate as mentioned, and Dakim has the always annoying tactic of constantly using Earthquake and Protect as a combo. Of course, Entei can't protect from that and there's always a chance of him dying!

 

[Terminus]

It was over a year ago, but all the ones the Boss had at the end of GoD were nigh on impossible. Had to to the fight 8 times to get everything.

 

[Blue Canary]

Smeargle. That thing dies in one hit.