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Here is a quick run through of how to get the "I Love Tails" achievement for playing as Tails 50 times.

Because it requires you to complete a full level and because failing a special stage zone is technically still completing it keep replaying Special Stage 5 in this fashion.

Sonic - Hold Right and X to Boost
Tails - Hold Left and Boost

If you only have one of you, with two controllers this can still be done by holding right and boost with Sonic. Just make sure you don't hit the first spring. As you can see in the video it pops up on the score screen.

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