Transgender representation on television and in film is better than ever, thanks to big names like Laverne Cox paving the way for new talent and big screen successes like Tangerine and The Danish Girl.

A symbol of society's increasing acceptance of trans people, more shows are now choosing to tackle issues – such as the complex, emotional process of transitioning and transphobic violence – that affect the transgender community head-on.

In the last two decades, however, transphobia has been visible in a number of our favourite mainstream films and TV shows - whether it's stereotyping of transgender women or poor-taste jokes. Here are some of the worst examples.

Ace Ventura: Pet Detective

One of the breakthrough films for Jim Carrey, Ace Ventura was a firm family-comedy favourite in the 1990s. It features, however, one of the clearest-cut moments of transphobia in Hollywood history.

Towards the end of the film, Ace Ventura discovers that female police detective played by Sean Young, Lois Einhorn – who he has killed – is actually the same person at Ray Finkel, a male character. When he finds out, he is so disgusted that he is sick in the toilet, brushes his teeth and sets fire to his clothes outside, before scrubbing himself in the shower.

Ace Ventura
Jim Carrey in Ace Ventura: Pet Detective (1994) Warner Bros/IMDB


One of the recurring comic themes in Friends is Chandler's estranged father, Helena Handbasket, a transgender woman played by Kathleen Turner. In one scene, words are exchanged between Handbasket and her ex-wife Nora, who scathingly points out Handbasket has "too much penis" to wear a dress.

Family Guy

Everybody knows Family Guy takes a dig at all groups, from women to people with disabilities - but this doesn't mean it's OK. There have been plenty of jokes about transgender people, most notably in the eighth season, when Glenn Quagmire discovers his father identifies as a woman called Ida. Brian and Ida spend a night together and after finding out Ida is a trans woman, Brian is violently sick in a lengthy – and tiresome – gag.

The Assignment

Yet to be released, the show has already been panned by trans rights advocates. Originally called (Re)Assignment and Tomboy, the film involves a male assassin who is subjected to a forced vaginoplasty and breast implant surgery – which is referred to as gender reassignment surgery – as punishment. Unsurprisingly, it has received a huge backlash.

Speaking to Rolling Stone, director Walter Hill said his intention wasn't to smear trans people. "I wouldn't make a movie that hurt transgender people. Some of them have had a tough time of it, and the last thing I want to do is make anyone's road harder," he said. "But look, I understand the concern. Is it lurid? Yes. Is it lowbrow? Well, maybe. Is it offensive? No. I'm just trying to honor the B movies that we grew up with."

Michelle Rodriguez in The Assignment
Michelle Rodriguez in The Assignment IMDB

Zoolander 2

This film is plentiful when it comes to bad jokes, but perhaps the worst was the lazy mockery of Benedict Cumberbatch's genderfluid character All. All appears to be a satire of androgynous fashion models, following the success of Serbian-born model Andreja Pejic, who became the first trans woman on the front cover of American Vogue in 2015, the year Zoolander 2 was released. In one scene, All is asked: "Do you have a hot dog or a bun?"

The 40-Year-Old Virgin

Another seemingly-innocent comedy, there is one major transphobic moment in this Hollywood blockbuster. Protagonist Andy is tasked with finding someone to lose his virginity to and his friends hire him a sex worker, who turns out to be trans – another unflattering stereotype.

Andy explains how he found out: "Because her hands were as big as Andre the Giant's. And her Adam's apple was as big as her balls."

Mike and Molly

In the fourth season, Mike and Molly meet Lousette, a trans woman – who they repeatedly misgender amid questions about "managing" her genitals. And this isn't the first time the show has come under fire for some dubious jokes, it has previously used the slur "she-male".

Family Guy
Brian finds out he has slept with a transgender woman YouTube

Naked Gun 33 ⅓

The 1994 comedy Naked Gun 33 ⅓ plays on the time-old trope that transgender people are to be mocked and riffs on the notion that trans people "hide" their true identity to deliberately "trick" others. The character Tanya Peters, played by Anna Nicole Smith, kisses detective Frank Drebin, played by Leslie Nielsen. When Tanya undresses, a shadow of male genitalia is seen on the wall behind. Visibly horrified, Frank runs off to throw up.

The Simpsons

There are many questionable moments passed off as comedy in the Simpsons when it first aired in the early 1990s – include many references to trans people as "she-male". Futurama has arguably features worse moments, particularly with the introduction of the character Hermaphrobot – who is one "upgrade" from being "more lady than [Bender] can handle".

Dude, Where's My Car?

This 2000 classic was panned for a number of good reasons, but like other comedies of the time, it plays on the tired trope of the transgender woman as a sex worker and criminal. One of the first characters the two protagonists encounter is Tania, a transgender stripper who turns out to be a thief.