Tokugawa Ieyasu

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    "If the cuckoo does not sing, wait until it will."

    Credited as the third unifier of Japan and the man who kickstarted the Tokugawa Shogunate that would rule Japan for over 200 years. Ieyasu has been around since the early era of Oda Nobunaga. Born named Matsudaira Takechiyo; his first claim of event in history is being the man who stabilized his clan's survival... by being a hostage for the Imagawa Clan. As a hostage, Takechiyo starts learning a lot, especially about the arts of war and later even changed his name into Matsudaira Motonobu, and later Motoyasu. When Imagawa Yoshimoto fell to Oda Nobunaga's might, Motoyasu declared independence, allied himself with Nobunaga and proceeds to strengthen his home base Mikawa, getting himself some powerful generals (including Hattori Hanzo and the Badass Honda Tadakatsu), then changed his name into Tokugawa Ieyasu.

    Ieyasu helped Nobunaga a lot in his quest to unify the land, and when Mitsuhide got Nobunaga dead, Ieyasu retreated through the Iga Province (helped by Hanzo), and planned a counterattack... only to find that Toyotomi Hideyoshi got there first in avenging Nobunaga and finished up his conquest. Ieyasu ended up becoming Hideyoshi's vassal as the latter successfully unified Japan.

    When Hideyoshi died, Ieyasu grew to become the most influental and powerful man in Japan. Lots of people didn't like how he looks like usurping Hideyoshi's place and eventually this leads into a huge battle in Sekigahara, with Ieyasu leading Eastern Japan, and Western Japan led by Ishida Mitsunari. Ieyasu scored a huge victory thanks to some luck and became the next Shogun. His last known activity was during the Siege of Osaka, whereas Sanada Yukimura managed to charge through to his camp and Ieyasu nearly had to fight for his life... until Yukimura declares that he's too tired... then dies due to battle wounds, prompting Ieyasu to praise him as 'Japan's Number One Soldier'.

    One thing Ieyasu is known the most is his patience and knowledge about deciding just when is the time to strike, and when not to. There's some saying that "Ieyasu won the country by running away." Talk about ironic. He also learns the Yagyu Shinkage-Ryuu from Yagyu Jubei (Muneyoshi was his teacher, and Munenori became his retainer).

    When compared to Nobunaga and Hideyoshi, we can say that Ieyasu is a less common victim of Historical Villain Upgrade. However, you will be more likely to see him upgraded into villainy when there are those who sympathized with either Sanada Yukimura or Ishida Mitsunari.

    Example of works featuring Ieyasu:
    • Kessen, in both the first and third game. For the first game, Ieyasu is one of the protagonist and can go either sympathetic or unsympathetic, depending on whoever is picked as protagonist (Him or Mitsunari). In the third game, he is forever a second banana to Nobunaga since Nobunaga survived Honnoji and is the main protagonist.
    • KOEI's Samurai Warriors. Ieyasu starts out as some sort of cowardly Fat Bastard Smug Snake NPC in the first game, but by the expansion, he grew some competence (despite still being NPC) and sympathy. And in the second game, he became playable, got a spear cannon for weapon and can be a Fat Gentleman.
    • Ieyasu is mentioned in Onimusha: Dawn of Dreams as Soki's uncle. However, Soki thinks he's just a useless lapdog to Hideyoshi.
    • In Samurai Deeper Kyo, Ieyasu is a literal Fat Bastard... until it's revealed that this fat bastard was just a Kagemusha. The REAL Ieyasu took the guise of Hattori Hanzo.
    • Capcom's Sengoku Basara has an... interesting take on Ieyasu. Early on in the series, he's a short, plump, impatient little brat; and while he's virtuous, he's also rather incompetent, relies too much on Tadakatsu, and gets kidnapped way too often. But in the third game, he grew up, took massive levels in badass and became one of the main protagonists.
      • In his first incarnation Takeda Shingen drives the point home (at least in the anime) by addressing him as Takechiyo, his childhood name he used before coming of age (Ieyasu is technically his adult name, though historically he changed his name to "Tokugawa Ieyasu" much later).
    • In Saber Marionette J, the Japoness is led by a man named Tokugawa Ieyasu. He looks like a normal old man usually, but flashback reveals that he's just as bishonen as the protagonist Otaru when he's younger.
    • Saihai no Yukue, an Ace Attorney-like game based on Sengoku era (by Koei) features Ieyasu as a Fat Bastard antagonist, while our protagonist is the Bishonen Ishida Mitsunari. Though, in the end, it's subverted that Ieyasu was suckered by the true villain of the series: Lady Yodo.
    • The Japanese campaign of Age of Empires III: The Asian Dynasties is about his rise to power, with help from the player character.
    • One of the few works where Ieyasu is arguably the villain would be in Futaro Yamada's The Kouga Ninja Scrolls, with Ieyasu pitting the warring Kouga and Iga ninja clans in a free-for-all simply to determine who among his grandchildren would ascend to the Shogunate, setting off the tragic events for all participants. The manga and anime adaptation of the story, Basilisk takes this Up to Eleven and Gonks him up.
    • Tokugawa is the leader of the Japanese civilization in the second, third, and fourth installments of the Civilization series of games; he is noted for being particularly isolationist in IV. He gets replaced by Nobunaga in V.
    • The character of Toranaga in James Clavell's novel Shogun is based on Ieyasu.
    • Bandai's SD Sengokuden Bushin Kourin Hen has depicted several Warring States characters in SD Gundam form, picking the three unifiers of Japan to make at a larger "deluxe" size. Ieyasu is the last of the deluxes and possibly the last model released.
    • Sengoku Otome presents a gender flipped Ieyasu as appearing sweet, but actually being the most underhanded character in the series. She's not opposed to cheating, and is actively planning to take the Crimson Armor for herself once Nobunaga completes it.
    • Ieyasu is the Big Bad of Brave 10 and thus far shows himself as a ruthless warlord.