Given that satire about life in America during the George W. Bush presidency is such a big part of the game, today it can feel like a product of a different era. In some cases this trope goes up to eleven as the game features or satirizes trends that were already going out of style in 2008.
- The game's soundtrack features reggaeton (which has its own dedicated station in the form of San Juan Sounds) and "ringtone rap", two flash-in-the-pan musical genres from the mid-2000s that had already more or less fizzled out by 2008.
- Speaking of radio stations, The Vibe 98.8 (the R&B radio station) features "Bump N' Grind" by R. Kelly in its soundtrack, something that would be flat-out inconceivable a decade later following the numerous sexual misconduct/abuse accusations against him, especially after the Lifetime documentary Surviving R. Kelly was released.
- The game really takes aim at the "bling" culture in America, something that died hard and quickly among the 2008 economic collapse, an event that was beginning to unfold when Grand Theft Auto IV was released. Much of the in-game media, alongside The Ballad Of Gay Tony focuses on the booming nightclub scene and the lives of celebrities, featuring parodies of socialites like Nicole Richie and Paris Hilton, with the in-game television airing a program based on Cribs.
- One of the in-game celebrities, Kerry McIntosh, is a clear parody of Britney Spears and her then-recent breakdown, referencing Spears shaving her head, her hospitalizations, and her hit-and-run charge, all of which are Played for Laughs. There's no mention of Spears' infamous conservatorship, which happened just months before the game released, and would later cause the public to re-evaluate her breakdown.
- The game's spoofing of politics in America feels pretty dated today given how the presidency of Donald Trump vastly transformed them in The New '10s. For example, conservative politicians in the game are hung-up about the gay rights movement over anything else, clearly dated to before the legalization of same-sex marriage in 2015. An obvious parody of Rush Limbaugh is one of the right's most prominent voices. Surprisingly, even though the game's setting is based on New York City, there is no Trumplica to be found (although a building heavily based on the Trump Tower called the Cleethorpes Tower is present and was indeed named after Trump within the game files). On the left side of the aisle, it's satire of liberal politics largely centers around Hillary Rodham Clinton, who at the time was already being supplanted by Barack Obama as the major power player on the left and was out of politics altogether a few years later. All of this exists among a backdrop of the War on Terror being the biggest political issue on everyone's mind, with the bridges to Algonquin and Alderney initially being closed off due to perceived terrorist threats.
- The Liberty City Police Department are depicted as over-saturating high-crime areas with several units and flying weaponized helicopters over the city, with the majority of the beat cops seen being overweight and weak. There's only brief mentions of Police Brutality, which would be mentioned far more commonly with the rise of the Black Lives Matter movement just a few years later.
- Most of the police cars and taxis are genericized Ford Crown Victoria, as the Crown Victoria effectively had a monopoly on those markets in the 2000s. The Crown Victoria was discontinued in 2011, however, and now most Police and Taxi fleets have retired them from service. In many cases, police departments replaced them with SUVs like the Chevrolet Tahoe and Ford Explorer, while yellow cab companies replaced them with minivans or hybrid vehicles like the Toyota Prius. It should be also noted how in the game, the yellow cabs dominate the market with no competition from ridesharing services.
- Similarly, the vehicles don't account for the boom in crossover SUVs, so the roads are full of large truck based SUVs, minivans and full size sedans, vehicles that have really dwindled in numbers since GTA IV's release. Of particular note is that a large SUV based off the Hummer H2 is commonly found on the road, even though Hummers had already fallen out of fashion by then thanks to the 2000s energy crisis, leading General Motors to state they were considering withdrawing the Hummer brand from sale in June 2008, two months after the game was released. Conversely, the game features a hybrid car based off the Toyota Prius that really only exists as a Joke Character to poke fun at the people who drive them and isn't commonly seen on the road. As hybrid and even full electric vehicles have become mainstream and the Prius has become a common sight on middle America's roads, the game's dismissive attitude towards hybrid vehicles is certainly dated.
- Even though it came out a year after the iPhone's release, the game only depicts old, candybar-style cell phones with the highest end phone in its universe that actually works being a parody of the BlackBerry, and the iPhone equivalent being something that doesn't work at all.note At one point Niko receives a color-screen cellphone from Playboy X, which features a camera and wallpaper settings but no internet access. The game also dismisses text messaging and picture texts as useless technology in commercials that parody Verizon Wireless' iconic 2000s "Can You Hear Me Now?" ads.
- The game's depiction of the internet is rooted primarily in the late 2000s. The main social media site is a parody of MySpace, which was already well on the way of being supplanted by Facebook by mid-2008. (Facebook's takeover would be addressed in Grand Theft Auto V, where attempting to access Myroomonline.net will show that the site has been shut down thanks to LifeInvader, the in-universe Facebook equivalent.) Other sites include spoofs of eHarmony, Classmates, Jamster, YouTube (back when the site was in its infancy and being plagued by DMCA strikes), Skype, and Second Life.
- If the player tries to visit the website littlelacysurprisepageant.com, they'll be greeted by a white page informing them that they've been caught by a police sting and an instant five star wanted level. This is playing off of the moral panic over child sex predators on the internet whipped up by To Catch a Predator.
- Eunux.net pokes fun at various things about Linux and its userbase, including its lack of game support. Starting in The New '10s, there is a huge push by Valve Corporation to fix this, and now thousands of PC games work on Linux operating systems, including the entire Grand Theft Auto series.
- Nerdy pedestrians can be heard saying "Wow! Two gigs of RAM!". Thanks to Windows Vista, this was already on its way to not being an impressive amount.
