Top 10 Creepiest Herbert Moments on Family Guy

We all try to keep our most prized possessions close to us, but Herbert seems to take it to a whole other level. In one of "Family Guy's" signature cutaways, Peter teaches a group of kids about pickpocketing when he spots Herbert a few feet away. He commands the kids to go after Herbert, and the old man does nothing to defend himself, instead giving away where he's "hidden" a small wad of cash. And it’s NOT in his wallet . . . Honestly, this guy will try ANYthing . . .

To any normal viewer, this seemed like a neighbor doing a favor. Longtime "Family Guy" viewers, on the other hand, saw this coming a mile away. In the season six episode "Play It Again, Brian", Herbert babysits the Griffin kids while Peter, Lois, and Brian take a vacation to a vineyard. Right from the start, Herbert threatens them (well, moreso Chris) with a slap if they backtalk. He even attempts to talk Chris into giving him a bath only to find himself getting one from Meg. Jeez, way to take one for the team, Meg.

This was either Herbert's most famous or infamous moment of the show. In the episode "To Love and Die in Dixie", the Griffins are placed under a witness protection program and must live in Texas until things clear up. However, upon their return, they find their answering machine has received over a hundred voice messages...all of them from Herbert. As the messages go on, his tone gets worse and worse, growing from his normal, creepy self to aggressive and threatening. How have the Griffins not filed restraining orders or left Quahog yet!?

How could Herbert possibly get creepy at something like a yard sale? Well, dear viewer, Herbert always finds a way. In Season Five’s famed episode “Road to Rupert”, the Griffins hold a yard sale where Chris sells his old clothes. Naturally, Herbert appears, asking about his hand-me-downs, and specifically about clothes that Chris wore during the hotter months of the year. In response, Chris shows him a used pair of shorts. It’s bad enough this guy hits on Chris on a regular basis, but to be desperate enough to buy old, sweaty clothes? That’s a whole new level of gross!

The episode “Movin’ Out” sees Chris get a new job at a convenience store, allowing Stewie to take over his newspaper route. Yep, you can see where this is heading… Herbert greets his new paper boy from his yard only to be met with Stewie’s typical vitriol. However, the old man’s response shows that unfortunately, the insult didn’t phase him - in fact, possibly the opposite. If we had any choice words for Stewie it’d be this - quit while you can, and don’t look back! Unfortunately, this would not be the last encounter, as we’ll see later on this list.

While we watched Stewie become a tanning addict in season five’s “The Tan Aquatic with Steve Zissou”, we also got a B plot that was just downright uncomfortable. Chris finds himself at odds with Kyle, a new paper boy who has stolen Herbert’s business and continues to bully Chris. Throughout the episode, Herbert greets Kyle in an overly interested tone and makes awkward remarks about his clothes. We’re really not quite sure why Herbert gets turned on by baggy shorts (or venomous remarks from Kyle), but we’d rather not have an explanation. How has no one called the cops on this guy?

At the beginning of the season nine episode “German Guy”, Peter and Chris set out to find Chris a hobby when they run into Herbert. Surprisingly, the conversation isn’t all that cringey, but just when we thought everything was okay, Herbert does something as Chris walks away - he asks God to let him sniff Chris’s hat. A strong breeze manages to blow the hat away and straight into his hands. Alas, this has only encouraged him ...Wait a minute, how did Chris not feel his hat fly off his head!?

It’s no surprise that when Herbert hires Chris and Peter to mow his lawn, he has other things on his mind. However, the job goes sour when Chris ends up doing all of the work while Peter plays games with Herbert inside. It isn’t long before Chris storms in to confront his dad, and the two begin fighting in front of Herbert. Of course, the old man does nothing to stop the fight, and it doesn’t help that Chris and Peter yell innuendos at each other. The whole thing ends with Herbert going out with a bang, and nope, there wasn’t any other way to describe that.

Over “Family Guy’s” twenty-plus-year run, we’ve seen a handful of Herbert’s fantasies where Chris is living with him (while wearing no shirt and sweaty shorts). Well, the creeper got his wish in season eleven’s “Chris Cross”. After Meg blackmails him for stealing from Lois’s purse, Chris runs away to go live with Herbert. During his stay, Herb does everything he can to get close to Chris . . . His dreams are shattered when he finds out just how messy and stubborn Chris can be, and he eventually kicks him out . . . fortunately for Chris!

Before we reveal Herbert’s creepiest moment, here are a few dishonorable mentions…

The Popsicle Stand

Going to a High School Prom

Resolving Chris & Kyle’s Fight

Hiding in Chris’s Closet

The “Safety Basement”

This season ten episode gave us a rather interesting short called “Point of Stew”, where viewers got to see the world through Stewie’s eyes. However, there are some things we wish we hadn’t seen. When a prank on Brian goes wrong, Stewie finds himself on a ride through town beneath his dog’s car. Along the way, he stops by a school bus full of kids and discovers Herbert underneath. There have been multiple times where Herbert shows how weak he is. Oh, but he’s strong enough to hold onto a bus!? That’s just downright terrifying!