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In the video game Final Fantasy V, the character Faris is the captain of a crew of pirates, dressing and presenting herself as a man.

In one of the more humorous scenes in the video game Final Fantasy VII, the protagonist, Cloud Strife, had to disguise himself as a woman in order to infiltrate a brothel.

In the first game of the Art of Fighting series, King, who later would become a household character and player's favourite, dressed up as a man in order to hide her real gender, because of a shameful loss she suffered in a martial arts tournament she entered in the guise of a man. It can be revealed that King is a woman if the player finishes her off with a special move, tearing up her shirt. Later on, it was no longer unknown to anyone that King is in fact a woman, but she keeps on using men's typical outfits.

In the Guilty Gear series, Bridget is a boy who looks like, is named after and dresses up as a girl, because the village in which he was born has a belief that male twins bring bad luck. As Bridget himself is a male twin, he underwent this makeover since his childhood.

In the Angelique series, the character Olivie is always seen in elaborate, flamboyant women's clothing, often accompanied by cosmetics and fancy nail art.

In Tokimeki Memorial, the character Rei crossdresses and attends school as a male. Her secret can be revealed in her love ending.

In StarTropics, Mike must crossdress to enter an all-women's kingdom.

In Legend of Zelda : Ocarina of Time, Zelda presents herself in a male form known as Sheik.

In Monkey Island 2: LeChuck's Revenge, Guybrush dons a pink gown.

In the Japanese comic book series Urusei Yatsura (1978-1987), created by Rumiko Takahashi and published by Shogakukan, a female character named Ryuunosuke wears a white shirt with the Chinese ideogram for "male" on the back (as well as on her pants), along with other male attire, as part of her father's misguided insistence that his child is a male. More recently, in the Japanese action comic Gunslinger Girl (2003), published in the United States by ADV, one female character, brainwashed to be an assassin, takes pleasure in wearing a men's-style suit and tie.

In Pokémon, James (Kojiro) frequently cross dresses and Ash (Satoshi) cross dresses to get lessons from Erika in series one.

Mulan featured the main character cross-dressing to fight in place of her aging father.

In Bobobo-bo Bo-bobo Don Patch and Bobobo frequently cross-dress (example, episode 29).

In I My Me! Strawberry Eggs, another Japanese anime, a man dresses as a woman with the help of his landlady in order to get a job at an all-girls' school.

Another Japanese title, High School! Kimengumi regularly features crossdressing antics from the five main characters.

In Slayers, most male characters are seen crossdressed to aid plot devices.

Tsubasa Kurenai in Ranma 1/2 is always seen in dresses and skirts.

Bugs Bunny occasionally engages in cross-dressing, usually to confound a foe. His transformation is typically so effective that his adversaries (especially Elmer Fudd), who moments earlier had been trying to kill him, are smitten by his "feminine charm." Elmer Fudd and Daffy Duck have also cross-dressed in some Warner Brothers cartoons.

Genesis Climber Mospeada was perhaps the first anime series to feature a regular crossdresser amongst the main protagonists. Yellow Belmont, a former soldier, crossdressed to avoid anti-soldier reprisals by the Invid and others, and eventually became an accomplished pop singer. Many were a fan of Yellow's, without realizing that Yellow was really a male.

In SpongeBob SquarePants, SpongeBob in four episodes is briefly portrayed in women's clothing which made him into a potential gay icon.

An entire genre of operatic roles, called "pants roles" or "trouser roles" or "travesty roles" exists,
sung typically by mezzo-sopranos, and on rare occasion by sopranos, demonstrates a trend of characters
who are men or boys being portrayed by women. The reasons for this run the spectrum from the ability of
a grown woman's developed voice being able to fill the theatre better than that of an actual young boy
(Cherubino in "The Marriage of Figaro," Hansel in "Hansel and Gretel", to the need for the character to be
other-worldly or unmanly (Orpheus in "Orfeo ed Euridice" and Prince Idamante in "Idomeneo," respectively),
to the simple idea that women in the era of Grand Opera's heyday typically wore voluminous dresses -
and to see a woman's legs clad in clingy trousers was quite appealing. Some opera singers are known
for specializing in these types of roles.