The Best Pokémon Games to Start With Are Still the Classics From 20 Years Ago

September 2026 · 4 minute read

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Published Sep 19, 2026, 9:00 PM EDT

Jason Venter is a long-time gamer from beautiful Oregon who has spent much of his life inside playing games or writing. He contributes to Polygon to share those passions, after previously freelancing at sites like IGN, GameSpot, GamesRadar, and HonestGamers, among others.

Part with some clams and play these proven classics

A Charmander with goggles trying to be intimidating but being cute instead. Image: The Pokemon Company

The Pokémon franchise from Game Freak is a revolving door. Someone is always going in for the first time, while someone else is on the way out. There’s a new mainline entry or remake every few years, which keeps interest levels high. Sooner or later, most of us cave and try a Pokémon game. Then we’re stuck in that universe alongside everyone else.

My own entry came with Pokémon Pearl and Pokémon Diamond. Those titles arrived in Japan on Sep. 28, 2006, two decades ago. And although plenty of newer titles have come along with ambitious new twists, those classic Pokémon games are still a perfect starting point, even 20 years later.

My game of choice was Pokémon Pearl. The cover art featured Palkia, a warrior lizard with sturdy legs and an extended neck. I wasn’t completely enamored with its design, but it interested me more than Pokémon Diamond’s Dialga, which more closely resembled a plant-eating dinosaur. I wanted the other monsters to fear my starter, not eye it as a possible addition to their lunch menu.

Besides those attractions, the games added a bunch of other new Pokémon to the mix. There were 107 new monsters in total, and players had to pick up both games if they wanted to “catch ‘em all” and complete their Pokédex. Either that, or they needed to trade with friends who owned the other version, using the Global Trade Station feature with the Nintendo Wi-Fi Connection.

pokémon diamond and pearl art Image: Game Freak, The Pokémon Company/Nintendo

In 2006, most of my friends weren’t playing Pokémon games. That didn’t stop the fun, though. I easily could have spent a bunch of time trading and battling with strangers, because plenty of other people picked up one or both titles. In fact, Pokémon Pearl and Diamond remain two of the most successful entries in the franchise, even now, with roughly 40 million copies sold between the DS and Switch versions combined. They outsold both their immediate predecessors and successors by millions of units.

For the solo player, Pokémon Diamond and Pearl offered other changes besides online play. Days now consisted of five chunks: morning, day, afternoon, evening, and night. That more detailed accounting of time gave players reason to stay longer in regions, hunting for rare Pokémon varieties instead of racing through zones on the way to the next gym. Another change related to attack types. These games featured three groups: physical, special, and status attacks. A fire- or water-based move might now fit within any of those groups, rather than always being physical.

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The setting also changed. Players explored the mountainous Sinnoh region (later featured in modified form in 2022’s Pokémon Legends: Arceus). Based on Japan’s northernmost island of Hokkaido, Sinnoh is an island with a mountain running through its center. There are several lakes on the surface, as well as a network of tunnels that give exploration a unique feel compared to previous games in the series.

When Pokémon Diamond and Pearl launched, players quickly took advantage of the online play, while also enjoying the improved visuals and the new Pokémon breeds. They were followed by the generation’s third game, Pokémon Platinum, in 2008. Platinum further expanded the Sinnoh Pokédex, added new characters to the story, and introduced a new dimension known as the Distortion World. It also made numerous small tweaks in other areas to improve the overall experience.

To play Pokémon Diamond and Pearl today, it’s no longer necessary to drag out your trusty DS and hunt down those old cartridges. In 2021, Nintendo released Pokémon Shining Pearl and Pokémon Brilliant Diamond, Switch remakes that faithfully reproduce much of what made the DS versions so compelling. You won’t get a completely authentic experience, but the convenience and improved graphics make up for it, especially since complete copies of the original versions now cost so much.

Two decades ago, Pokémon Pearl and Pokémon Diamond officially introduced me and many other players to the wonders of Pokémon by providing an exciting new region to explore, robust online features, and new features that evolved the classic experience in satisfying new ways. If you’re looking for a starting point on your own Pokémon journey, you could do much worse.