Man, this web server is a sad, sad sack. It goes on and on and on, at times blaming itself and at times blaming you for expecting too much of it. Buck up!
I shouldn't be saying this, but this is the best 404 page on this list. You could click away to some other site now. It kills our time-on-site stats, but I'm just trying to shoot you straight. This error page lets you play Pac-Man inside a giant 404-shaped level. I found it to be more fun than the standard Pac-Man level, even.
This one's definitely elaborate and artsy. Wait for the subway car to show up, then click on one of the open doorways to climb aboard. Once inside, you're treated to a sleeping passenger and a girl who likes to take photos of stuff. It feels like a scene in a '90s-era full-motion adventure game.
This goat is upset that it's reached an error page. It shows its frustration by screaming like a human. Then the whole scene repeats itself. You'll laugh at the scream more than once, assuming you find it funny the first time. Disclosure: I found it funny the first time.
Lloyd Christmas Can't Believe What He's Seeing
No! No, no, no, no, no!!!
This error page features a tiltable 404 made of luminescent, bubble-like circles. Click on a section of one of the numbers and watch a bunch of the circles go flying, only to repopulate moments later. You can get trapped here for a while if you're not careful.
Can't read what this error page says? Who cares?! Something's gone haywire, and the two stick figure construction dudes respond by dancing. With a page title like "Ooopps... 404" and its jibbly-yup-yup (new term!) music, this is the most wonderfully weird error page on the list.
An homage to Jurassic Park's famous hacking scene, here's Dennis Nedry (Wayne Knight in real life -- arguably most well-known as Newman on Seinfeld) scolding you for touching his keyboard. Hint: type "reboot system" three times to get things moving.
This Could Go On For Days
This travel site's 404 page features a soothing, endlessly watchable sunrise-sunset-moonrise loop that delicately blends background hues together, bringing out the stars at night and blue skies during the day.
Can I Leave Now?
Appropriately titled "The Most Awkward 404 Not Found Page on the Internet," artist Steve Lambert's error page features an excruciatingly long video of him explaining that you don't have to hang around the error page if you don't feel like it. Bonus points if you watch the whole thing. I did.
More Like Homestar Ruiner
Though not technically a 404 page, this Homestar Runner cartoon about the site crashing has aged well after all these years. The site does have an actual 404 page, which you can find here.
"We've Got Motion!"
And last but certainly not least, the video embedded in this 404 page for Nosh.com's site is no longer working (irony!), but the original (embedded above) that used to play there is truly outstanding.