Friends was a cultural phenomenon that TV audiences are still binge-watching now, more than 20 years after its final episode. But it’s also a product of the 1990s, when sitcom writing was more reckless and less responsible. And as Zoë Kravitz recently pointed out, Friends certainly shows its age.

In a recent interview with People about her new ’90s-set movie Caught Stealing, Kravitz said she’s nostalgic for the decade, except when it comes to “super homophobic jokes on mainstream television.”

“If you watch Friends now, you’re like, ‘Whoa,’” she added. “Like, things that aren’t punchlines are punchlines. It’s wild.”

She’s not wrong, as you’ll see below. And yes, Friends was progressive in some aspects — it featured a same-sex romance from the jump, for example, and it depicted interracial relationships and casual sex without judgment. And perhaps there’s an argument to be made that the six lead characters and their narcissistic, toxic, fragile, biased traits are the punchline. But you still can’t excuse away Friends’ worst transgressions, including the following fails — our picks for the sitcom’s most offensive moments, presented chronologically.