Chessmaster is a chess playing computer game series which is now owned and developed by Ubisoft. It is the best-selling chess franchise in history, with more than five million units sold as of 2002^[update].

The Chessmaster chess engine is called The King, written by Johan de Koning of the Netherlands. It was introduced in Chessmaster 4000; earlier releases featured a chess engine written by David Kittinger.

According to the September 2009 Swedish Chess Computer Association (SSDF) rating list, Chessmaster 9000 has an estimated Elo rating of 2718 on an Athlon-1200 PC. If multiple versions of other engines are stripped out of their list, Chessmaster 9000 ranks 14th among all engines tested. As of May 2008^[update], Chessmaster 9000 remains the most recent version rated by the SSDF. Another rating list, CCRL, places Chessmaster 11th Edition in 24th place on its December 2009 list.

The King engine allows users to create new playing styles, also called "personalities", by manipulating several dozen different settings, such as King Safety, Pawn Weakness, Randomness, Mobility and others. Individual piece values can also be adjusted. Chessmaster 9000, for example, features over 150 different personalities ranging from International Grandmaster strength down to Stanley, who is described as a monkey and plays what are essentially random moves.

Nicholas Nip (born March 10, 1998) is a United States Chess Federation (USCF) National Master (NM). In 2008, he became the youngest USCF Master in history, obtaining a rating of 2207 at the age of 9 years, 11 months and 26 days, a record that was surpassed in 2010 by Samuel Sevian.

Nip's feat broke the record held for a decade by fellow chess prodigy Hikaru Nakamura. However, Nip's record was not without controversy because matches were included in the rating calculations, prompting allegations of manipulation. Since accomplishing the record, Nip no longer plays chess, and due to his inactivity no longer appears on the bi-monthly top 100 lists for his age.

On April 21, 2008, Nip played ten simultaneous games on Live with Regis and Kelly. He defeated nine and had one draw.