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I have seen videos where Tails grabs Sonic and is able to fly carrying him. I have tried several key combinations but am unable to get it to work. How can I do this?

This is what it looks like, although it can be done besides this boss battle:

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My memory is quite hazy, so I'm quite possibly wrong. I seem to remember, though, that this was only possible when playing with two players, where the second player is controlling Tails –  Dave McClelland Dec 2 '11 at 14:02
    
Playing as Tails also has other advantages: dorkly.com/video/22718/dorkly-bits-tails-cant-die –  agent86 Dec 2 '11 at 15:37
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up vote 10 down vote accepted

You can only do this if you are playing in Sonic & Tails mode. You need to at least have a second controller if you're playing by yourself. You need to make Tails fly by having him jump in the air, then hit the jump button again in mid-air. He'll then start flying and you need to keep hitting the jump button to make him ascend or release it to descend. After about 8 seconds on the ingame clock, he'll descend to the ground again because he's "tired." You can also kill enemies if you hit them with your tails.

While he's in the air, you can either have him fly over Sonic to pick him up or have Sonic jump up to grab his hands. Tails will move slower because of Sonic's weight. Note you can also do this underwater, as Tails can "swim" then, but you can't ascend while hanging onto Sonic.

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Probably goes without saying, but this also works in Sonic 3 & Knuckles. –  Shinrai Dec 2 '11 at 15:40
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For swimming have sonic keep jumping, just don't miss catching him! –  George Duckett Dec 2 '11 at 20:59
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This is only possible if you have a second player who is controlling Tails. They can then pick Sonic up and you can fly.

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-1. One skilled player holding two controllers at once can use Tails to pick Sonic up. See FAE's answer. –  unforgettableid Jan 1 '13 at 1:49
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