Tony Hawk's Pro Skater HD is a skateboarding game that includes remastered levels from Tony Hawk's Pro Skater and Tony Hawk's Pro Skater 2. The game itself is built from scratch with an entirely new engine. It includes many of the modes and gameplay features from previous Tony Hawk games and supports online multiplayer (limited to the console versions) for up to four players. The core gameplay is to complete tricks and objectives to score points and cash and to unlock more of the game. Objectives are based on achieving a certain score, collecting the letters S-K-A-T-E and finding a hidden DVD. The selection of tricks is limited to those in the first two games of the series where the levels are also borrowed from and new tricks introduced in later games in the series are not included.

Big Head Survival is a new game mode where the character's head gradually inflates throughout the game, like a balloon. In the Xbox 360 version that supports avatars as characters this is shown through a balloon the skater has in tow. To prevent it from popping, combos need to performed to decrease its size. The Hawkman game mode is borrowed from Tony Hawk's Project 8 and requires the skater to collect pellets with specific moves. The Graffiti mode returns where the skater can colour the environment through tricks. With two players a better score overrules the initial player's colour.

The rosters of skaters includes a mix of known people as well as fictional characters.

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