- The Helmet of Date Masamune was an inspiration for the costume of Darth Vader of the Star Wars trilogy.
- Date Masamune has been featured in several video games including Koei's video game Kessen series (where he is a relatively minor officer), and Inindo: Way of the Ninja as the daimyo of the Rikuchu province.
- In Samurai Warriors, he is depicted as a young and hot-headed ruler who is chaotically interrupting the battles of other warlords, usually attacking multiple armies at once. His weapon in the first game is a pair of bokken. In the second game, he now looks a little older, though still with the iconic crescent-moon helmet, with his weapons changed to a western-style sabre and a pair of pistols. He frequently expressed ambitions to explore the world beyond Japan, and acquire new, foreign technologies. In the first game, Date's childhood name, "Bontenmaru" is the name of one set of his weapons. In the third game, Masamune has been aged even further, with longer hair and a more stylish costume. In this expansion, he has more of a friendship with Saika Magoichi and Naoe Kanetsugu, and still expresses his desire to explore the world beyond Japan. Masamune also appears in the related series Warriors Orochi, where he is an officer for Orochi's forces, but is unlockable in the 5th Gaiden for Shu Han. With the help of Xing Cai and Zhu Rong, Magoichi Saiga defeats Masamune, and convinces him to join Shu's quest to save Liu Bei. In the sequel, however, he returns as a permanent member of Orochi's forces. He also has a dream mode stage, where he teams up with Sima Yi and Mitsunari Ishida.
- In the manga series Samurai Deeper Kyo, Date Masamune (referred to in the series by his childhood name, Bontenmaru) is a member of the Shiseiten and former follower/rival of the main character Kyo. In the series, he is depicted as a tall, muscular, and physically imposing man with a heart of gold. Like his historical version, he wields a wooden sword as his primary weapon and can perform incredible feats of swordsplay with it, but is an even stronger fighter when unarmed. As a member of the Shiseiten, he goes by the name "Bontenmaru".
- In the anime series Yoroiden Samurai Troopers, the character Date Seiji is a descendent of Date Masamune. Seiji wears his hair covering one eye, and is at one point asked by Hashiba Touma if he does so because he is related to the One-Eyed Dragon.
- Capcom's highly successful hack-&-slash series Sengoku Basara, includes Date Masamune as one of the main characters. In Basara, a distinguishing trait of Date Masamune is his usage of Japanese-style English, or Engrish. Masamune is portrayed as a brazen young lord bent on having fun while conquering the country, dressed in blue and black with a tsuba as an eyepatch over his right eye as well as the historically accurate golden arc on his kabuto. He is also known in-game by his nickname, the One-Eyed Dragon (Dokuganryu). He is also depicted in a constant love-hate relationship with Sanada Yukimura, although there is no clear historical record to suggest such a relationship ever existed.
- Masamune also appears in the strategy game Shogun: Total War as a general in the Uesugi army but not until later in the game (around 1580). He also appears as the leader of the Date Clan in the Samurai Warlords Mod (aka the Shogun Mod) for Medieval Total War.
- He is also one of the Leaders (a class of Samurai) in Throne of Darkness.
- Date Masamune was also the main subject of the Japanese network NHK's taiga drama Dokuganryu Masamune (One-eyed Dragon, Masamune) in 1987, starring the then young Ken Watanabe as Date Masumune. To-date, this series is the highest rated NHK Taiga drama.
- In the Thomas Harris's novel Hannibal Rising, Hannibal Lecter's aunt, Lady Murasaki, is said to be a descendant of Date Masamune. It is one of Masamune's swords that Lecter uses to commit his first murder by killing a butcher named Paul Momund for insulting Lady Murasaki because she is Japanese.
- In Age of Empires III: The Asian Dynasties, Daimyo Date Masamune is available as a daimyo unit. In the game, he is available with Shogunate wonder, only for Japanese civilization. Daimyos can receive shipments and train troops, while they are a powerful hand cavalry unit. They also provide an attack boost to nearby troops.
- In the eroge Sengoku Rance, the youkai king of Oushuu is Dokuganryuu Masamune. "Dokuganryuu" is "One-Eyed style" and also the nickname of Date Masamune, "One-Eyed Dragon".
- Masamune also makes an appearance in several smaller manga series such as Brave 10 and Neo Dragoon, as he is a popular figure within Japanese history and culture.
- Date Masamune also appears in Sengoku Otome: Momoiro Paradox as a gender-switched version of his real-life self
- A hat similar to the Kabuto worn by Date Masamune is obtainable in Team Fortress 2, called the "Samur-Eye". It is wearable by the Demoman, who is also missing an eye.
- In the recent video-game spin-off anime series, Sengoku Paradise Kiwami, Date Masamune is dressed in purple outfit instead of blue.
His voice actor, Kakihara Tetsuya also sang the opening song 「リターン乱世独眼竜」 "Ritān Ransei Dokuganryuu", which is related to his nickname 'Dokuganryuu'.
- Professional wrestler DJ Nira wrestled as Masamune for the Dramatic Dream Team promotion on February 10, 2013.
Read more about this topic: People Of The Sengoku Period In Popular Culture
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