Hilarious In Hindsight / Grand Theft Auto IV

• Princess Bubblegum, eh?
• The I'm Rich Show Within a Show, features a guy named Tony Mctony, who is a 5 foot, rich African American male who brags about wasting his money on sports cars and pimping out his mansion. He even has an official logo, TMT. Anyone who follows boxing, knows that TMT is the label for superstar boxer Floyd Mayweather's Jr. business, The Money Team, which came about years after the game was released and before Floyd changed his nickname from 'Pretty Boy' to 'Money'. Floyd is even known for buying a lot of sports cars and pimping out his mansion in Vegas, which he shows off to the fans through online pics and videos. He is also 5 foot tall.
• One of the many in-game websites is a fan page for tablets, essentially a massive Take That! at the early 2000s incarnations of the devices, which were bulky, hot, and had abysmal performance and worse battery life. Fast-forward to today, and tablets (and phablets) are so popular that some are seriously predicting that in the longer run they may well kill off traditional PCs.
• If the player tries to visit the website littlelacysurprisepageant.com, they'll be greeted with a white page informing them they've just been busted in a police sting and an instant five star wanted level. While it was originally spoofing the moral panic about child sex predators on the internet whipped up by To Catch a Predator, it has taken on a new dimension in the wake of the FBI MoneyPak Ransomware, which seems to have been specifically designed to target people who are visiting parts of the internet they shouldn't be.
• U.L. Paper associating homosexuality with the in-universe FBI, if Clint Eastwood's depiction of the most famous Director of the FBI is to be believed.^note Not to imply that the film was the first to propose the theory that J. Edgar Hoover was gay.
• The game includes a vehicle manufacturer named Pegassi, which is a composite of Lamborghini and Ducati. Four years after the release of the game, Lamborghini acquired Ducati, making this a case of Accidentally-Correct Writing.
• The fact that the game has an entire station devoted to reggaeton. This one is hilarious because of how much the music industry has tried to forget about the "reggaeton bubble," but it also illustrates just how long the development process can take. Reggaeton was enormous on US airwaves in 2005 and 2006 when Rockstar licensed its music, but it was a different story by the time the game came out. Rockstar picked the wrong horse there. Though given the fact that Reggaeton blew up again in the late 2010's, perhaps Rockstar were just a decade too early.
• Jodeci's "Freek'n You" can be heard playing on The Vibe 98.8. It wouldn't be the only time the song was played in a setting revolving around crime, drug trades, and the mafia.