How Pokémon Games in Order of Generation Changed Everything (and Where to Start Now)

Honestly, trying to explain the timeline of Pokémon games in order of generation to someone who didn't live through the 90s is like trying to explain why we used to carry around heavy plastic bricks that ate AA batteries. It’s chaotic. It’s nostalgic. It’s a massive part of gaming history that somehow survived the transition from black-and-green screens to massive open-world 3D environments.

Satoshi Tajiri’s dream of catching bugs in the woods didn't just become a hobby; it became the highest-grossing media franchise on the planet. But if you're looking at the list of nearly 30 core titles, it gets confusing fast. You've got remakes, third versions, and "Ultra" sequels that aren't actually sequels.

Let's break it down.

The Foundation: Why Pokémon Games in Order of Generation Matter

The "Generation" system isn't just marketing fluff. It’s a technical boundary. Each new gen usually introduces a new region, a fresh batch of monsters, and—most importantly—a shift in the underlying code that often makes backwards compatibility a nightmare.

Generation 1: The Kanto Era (1996–1999)

This is where the obsession started. Red, Blue, and Yellow (or Red and Green if you were in Japan). These games were held together by digital duct tape and prayer. You had the 151 original Pokémon, the Kanto region, and a combat system that was... well, it was broken. Psychic types were essentially gods because their only weakness—Ghost—didn't actually have any strong moves to counter them.

Think about it: Lick was the only Ghost move that dealt consistent damage. It was weird.

But the simplicity worked. You fought eight leaders, beat your rival (who was always a bit of a jerk), and caught Mewtwo in a cave. It set the template every single game has followed for nearly thirty years.

Generation 2: The Johto Expansion (1999–2002)

Gold, Silver, and Crystal are often cited by "Gen-wunners" as the peak of the series. Why? Because Game Freak did something they’ve rarely done since: they let you go back to the previous region. After beating the Johto Elite Four, you realized half the game was still waiting for you in Kanto. It felt massive.

This generation introduced:

The Day/Night Cycle: Pokémon appeared based on the actual time of day.
Held Items: Giving your Pokémon a Berry to hold changed the competitive meta forever.
Two New Types: Steel and Dark were added specifically to nerf those overpowered Psychic types from Gen 1.
Shiny Pokémon: The Red Gyarados at the Lake of Rage was the first taste of a dopamine hit that players are still chasing today.

The Technical Leap and the "Great Split"

Generation 3: Hoenn and the Game Boy Advance (2002–2006)

Ruby, Sapphire, and Emerald brought color—real, vibrant color—to the series. But it came at a cost. For the first time, you couldn't transfer your old Pokémon from the previous games. This broke hearts.

However, Hoenn introduced Abilities and Natures. Suddenly, two Pikachus weren't the same. One might be "Modest" and better at Special Attacks, while another was "Jolly" and faster. This added a layer of math to the game that turned Pokémon from a kids' RPG into a legitimate esport. This era also gave us the first remakes: FireRed and LeafGreen.

Generation 4: Sinnoh and the Physical/Special Split (2006–2010)

Diamond, Pearl, and Platinum on the Nintendo DS changed the literal mechanics of how we fight. Before this, whether a move was Physical or Special depended entirely on its type. All Fire moves were Special; all Ground moves were Physical. In Gen 4, they finally realized that "Fire Punch" should probably be Physical. It changed everything.

We also saw the introduction of Global Link. You could finally trade with someone in Tokyo while sitting on your couch in London. It was revolutionary at the time, even if the Nintendo Wi-Fi Connection was notoriously clunky. HeartGold and SoulSilver also landed during this gen, which many fans still consider the greatest Pokémon games ever made.

When Pokémon Started Taking Risks

Generation 5: Unova and the Soft Reboot (2010–2013)

Black and White were controversial. Game Freak decided you couldn't use any old Pokémon until you beat the main story. It was a bold move. They wanted to recreate the feeling of playing Red and Blue for the first time.

The story was also surprisingly deep. It asked: Is it actually okay to keep creatures in balls and make them fight? N, the antagonist, was a complex character who genuinely believed he was doing the right thing. This was also the only time we got direct sequels—Black 2 and White 2—rather than a "third version" like Emerald or Platinum.

Generation 6: Kalos and the 3D Shift (2013–2016)

X and Y moved the series into full 3D on the 3DS. It looked gorgeous, but it felt a bit "easy" to some veterans. This generation gave us Mega Evolution, a temporary power boost that made older, weaker Pokémon like Beedrill or Mawile viable again.

It was pure fanservice, and people loved it.

Generation 7: Alola and the Death of Gyms (2016–2019)

Sun and Moon ditched the traditional Gym structure for "Island Challenges." It felt like a vacation. They also introduced Regional Variants—like Alolan Exeggutor with the incredibly long neck—which breathed new life into the original 151. Z-Moves were the big gimmick here, essentially "super moves" you could use once per battle.

The Modern Era: Switch and Open Worlds

Generation 8: Galar and the Wild Area (2019–2022)

Sword and Shield were the first mainline games on a home console (the Switch). The "Wild Area" was the first time we saw Pokémon wandering around in the tall grass instead of just appearing as random encounters.

Then came Dynamaxing. Making your Pokémon the size of a skyscraper was visually cool, but the real star of this generation was actually a spin-off: Pokémon Legends: Arceus. It changed the catching mechanics and paved the way for the future.

Generation 9: Paldea and True Freedom (2022–Present)

Scarlet and Violet are the current peak of Pokémon games in order of generation. They are fully open-world. You can go anywhere, tackle gyms in any order (though the levels don't scale, which is a bit of a bummer), and ride a legendary dragon like a motorcycle.

The "Terastal" phenomenon allows Pokémon to change their type mid-battle. It’s the most complex competitive mechanic yet. Despite some technical hiccups and frame-rate drops that drove the internet wild, the sales numbers proved that the hunger for Pokémon hasn't slowed down one bit.

The Weird Logic of Remakes and Sequels

If you're trying to play through the Pokémon games in order of generation, you have to decide: do you play the originals or the remakes?

Most experts—and honestly, anyone with eyes—will tell you to play the remakes. Omega Ruby is objectively a more streamlined experience than the original Ruby. However, there's a certain "crunch" to the original Game Boy audio and the limited color palettes that the 3D models just can't replicate.

There's also the "Third Version" problem. If you want to play Gen 4, should you play Diamond or Platinum? The answer is almost always the later version. Platinum fixed the agonizingly slow surf speed and added a whole extra dimension (The Distortion World).

How to Actually Play Them Today

The difficulty isn't the games themselves; it's the hardware. Nintendo is notoriously protective of its back catalog.

Switch owners can play Gen 8 and 9, plus the Brilliant Diamond/Shining Pearl remakes and Let’s Go Pikachu/Eevee.
3DS owners used to have access to almost everything via the Virtual Console, but with the eShop closed, those digital versions of Red, Blue, and Gold are harder to get legally if you didn't buy them already.
Physical copies of older games like Pokémon HeartGold or Pokémon Platinum have skyrocketed in price. We're talking $100+ for just the cartridge in some cases.

The "best" way to experience the evolution is to start with a remake of an early gen, then jump to a modern title to see how far the "Quality of Life" features have come. Going from the modern "Auto-Heal" button back to manually clicking through menus in 1998 is a culture shock.

Actionable Insights for Your Journey

If you're diving into the series for the first time or returning after a decade-long hiatus, here is how you should approach it:

Don't feel pressured to start at Gen 1. While it's the beginning, the mechanics are archaic. Pokémon FireRed or LeafGreen (Gen 3 remakes) are much better starting points for the Kanto story.
Focus on the "Third Versions" or Sequels. If you have the choice, always pick Emerald over Ruby/Sapphire, Platinum over Diamond/Pearl, and Ultra Sun over the base Sun. They are essentially the "Director's Cut" with more content and fewer bugs.
Use the Pokémon Home app. If you plan on playing through multiple generations, this cloud service is the only way to move your favorite team members from the 3DS era all the way up to the current Switch games.
Embrace the Regional Variants. Don't just stick to the Pokémon you recognize from the 90s. The newer designs often have much more interesting typing and abilities that make the modern games way more tactical.
Check the Version Exclusives. Before buying, always look up which Pokémon are exclusive to which version. You don't want to buy Scarlet only to realize your favorite Pokémon is stuck in Violet.

The series is a slow burn. It's about the journey across the regions, watching the sprites turn into polygons, and seeing a simple bug-catching game evolve into a global phenomenon. Whether you're starting with a pixelated Charmander or a high-definition Fuecoco, the core "gotta catch 'em all" spirit remains exactly the same.