Skateboarding slang for a heelflip — a trick in which the skater flips the board with the heel of the back foot, causing it to rotate along its long axis. The '-ie' diminutive shortening is typical of skate slang. Also sometimes used to refer to shoes with a wheel in the heel (Heelys), though the skateboarding sense is primary in this context.
He landed the heelie cleanly on his third attempt.
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Regional slang from around the English-speaking world — British, Australian, Irish, Caribbean, Nigerian, Filipino, AAVE, and the hyphenated-English dialects that make the internet sound local.
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(skateboarding, slang) heelflip.
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