As other shows airing right now are changing with the times, Family Guy struggles to shake off the shackles it’s worn since 1999. After all, the series was founded on shock value satire and intentionally offensive jokes, and a whole generation was raised on this humor.

Just earlier this year, the showrunners claimed they would “phase out” homophobic jokes. It remains to be seen whether or not that’s true. While the show’s tried to rectify past errors, it’s only after accumulating twenty years worth of objectionable jokes. We can’t discuss every single one, but here are ten that have aged poorly.

Anything Herbert Says

Quahog is full of eccentric, recurring characters, and one of the most notable is someone who has overstayed his welcome. Not living too far from the Griffins’ house is John Herbert, an elderly man Chris interacts with regularly.

What’s so strange about him? Well, he’s a pedophile, to put it bluntly. The show makes no qualms about addressing that either. One joke even in context—“You know, Chris, all my life, I’ve wanted to see you locked in a basement. But now that it’s happened, all I want to do is get you out!"—will make anyone cringe.

Bill Cosby

Family Guy has never been too kind to Bill Cosby, even before the world learned of the comedian’s history of drugging and taking women against their will was made public. And, after it became common knowledge a few years ago, Family Guy continued to go in on Cosby with no remorse.

Though, at some point, it became unclear if jokes targeting Bill Cosby were actually helping the conversation that needed to be had—sexual assault was not funny. One shocking moment was when the series reimagined the Bill Cosby Show opening. In it, Cosby drugs his costars and then some.

Tricia Takanawa

Race has always been a free-for-all opportunity for the show. The number of times the series was offensive about race can’t even be counted on one hand much less twenty.

For example, Reporter Tricia Takanawa is a racist caricature. Not only is she voiced by Alex Borstein—an actress with a history of playing Miss Swan on MADtv—Tricia is an embodier of stereotypes about East Asian people’s sexuality and culture. When Tricia interviews David Bowie, she succumbs to her carnal urges and proclaims, “I’ll take you home; I’ll make you fish ball soup.” It gets only worse from there.

The Death of Daniel Karven-Veres

The writers revel in their edgy sense of humor that often earns more gasps than genuine laughs. But at what point is the line crossed? In “Stewie Loves Lois,” Stewie unleashes a brutal throwaway joke whose origin people might not be aware of.

First, some background information on why it’s messy. In 2000, Ursula Karven’s four-year-old son Daniel was attending musician Tommy Lee’s son’s pool party. Daniel then drowned, and Tommy was accused of negligence. Lee was eventually cleared of wrongdoing. When Lois is ignoring Stewie’s suicide attempt, he says, “What is this, a Tommy Lee pool party?” Yikes.

Why Peter Only Has Two White Shirts

When Family Guy’s writers land its sight on a target, they shoot to kill. Meaning they will obsess over the subject matter or person ad nauseam.

In later seasons, the show was invested in reminding viewers actor Michael J. Fox has Parkinson’s disease. One joke that is more awkward now than before is from the episode “Tiegs for Two.” In the cutaway, Peter explains why he only has two white shirts. It’s a protracted monologue where it seems like the show is trying to feign humanity towards Fox. Then they go ahead and show the offensive clip anyway. Quelle surprise.

Quagmire’s Abused Sister

The show was slowly shifting in the right direction with “Screams of Silence: The Story of Brenda Q.” Previously, Quagmire’s sister’s abusive relationship was introduced as a gag to shame Brian. The sister, Brenda, later returned in season 10 for a very special episode. She was still being abused by her boyfriend Jeff, and, after she accepted his proposal, Quagmire planned on killing Jeff.

The episode almost works, but there are jokes about the victim. Even ones more or less criticizing Brenda for not leaving Jeff. The story’s heart was in the right place, but the execution is still amiss.

Child Harm

As we learned in season 7’s “The Juice Is Loose,” the Griffins apparently had another son named Peter, Jr. At the aforesaid infant’s grave, Peter says, “I’m sorry, Lois. I thought if I shook him enough he’d stop crying. I was kinda right.”

This attempt at gallows humor is similar to Stewie’s demand of “Shake me like a British nanny” in “Mind Over Murder.” The latter is a direct reference to British au pair Louise Woodward, who was convicted for shaking an 8-month old to death. The only thing shocking about these jokes is anyone would laugh at them nowadays.

Quagmire’s Predatory Habits

Something definitely isn’t right with your show if there once a petition asking you to stop writing jokes about sexual assault. And, in light of the important #MeToo movement, the show said they would address Quagmire.

Well, historically, Quagmire was prone to taking women without their consent. He drugged them, and he even held a number of them captive against their will. In “Quagmire’s Mom,” he almost experienced the consequences of his actions after unknowingly hooking up with an underage female character. Instead, he got off without serving any time. Nevertheless, jokes revolving around Quagmire’s heinous behavior simply aren’t funny.

Antisemitism

The original seasons of Family Guy had the pleasure of skirting by without too much flack—mainly because the audience was comparatively small. That didn’t stop them from getting into trouble for the season 3 episode “When You Wish Upon a Weinstein.” Or rather, they could have gotten into trouble had Fox actually aired it.

The network opted to not show the episode out of fear of it being antisemitic. With lines like “I’m sorry, Lois. I just wanted our son to be Jewish so he’d be smarter,” Fox’s concerns were valid. Nonetheless, it was instead aired on Adult Swim.

Transphobia

We first met Glenn Quagmire’s father Dan in the aptly titled season 8 episode “Quagmire’s Dad.” The audience was led to believe Dan was gay. The truth was Dan, now Ida, had come to Quahog to have sex reassignment surgery. The operation is a success, but Quagmire is having difficulty accepting Ida.

Meanwhile, Ida has a one-night stand with Brian. When Stewie informs the unaware Brian that Ida was transgender and was Quagmire’s parent, Brian vomits non-stop for half a minute. By today’s standards, the episode is hard to watch. The more recent “Trans-Fat” episode handled the topic better, though.