The best mid-generation game to start with: Dragon Quest V
Play it on: iOS, Android, Nintendo DS
Pros
While the quality of video games stories is often open to interpretation, I’m here to argue that Dragon Quest V (1992) has the best narrative of any game in the Dragon Quest series. It’s not so much that Dragon Quest V is a gripping tale full of twists and turns you’ve never seen anywhere else. Rather, it’s because the game is a beautiful reflection of our journeys through life, and the people we choose to share our adventures with. It’s a quest that spans the innocence of childhood all the way into the challenges of parenthood, and every step of the way feels human and relatable, despite the game’s fantasy setting.
It’s not just a reflective narrative that makes Dragon Quest V great. Dragon Quest V uses its life-spanning framework as a tool to start simply at the outset and introduce deeper game mechanics as you go. You can also catch and recruit monsters to use as party members, which is wildly innovative for the game’s time. Remember, Dragon Quest V originally came out in 1992, almost four years before Pokemon would change the world in 1996. Dragon Quest V embodies so much of what makes Dragon Quest great while offering so much more, making it a perfect starting place for those who have love for ‘90s and 2000s era RPGs.

Cons
If you don’t have love for ‘90s and 2000s era RPGs, Dragon Quest V can take some time to get used to. You’ll contend with random encounters in dungeons and on the world map alike, and the game can feel incredibly linear at times. It’s a little hard to play this one these days too, as you’ll need to play the mobile port if you’re not sitting on the Nintendo DS cart. While the mobile port is generally quite good, some may feel turned off by the prospect of playing a game with their thumb in portrait mode.

If you like Dragon Quest V
Dragon Quest IV, V, and VI were all remade courtesy of ArtePiazza (the team behind the 2023 remake of Super Mario RPG), so each game shares the same “vibe” even if they each have some fundamental differences. I’d specifically recommend Dragon Quest IV for fans of Dragon Quest V, as it also features a unique narrative that follows the game’s supporting heroes before the protagonist takes center stage. If you want an even simpler, but still engrossing RPG to start the series with, I’d actually recommend starting with Dragon Quest IV
Beyond that, I’d point Dragon Quest V fans towards Dragon Quest VIII and XI, but we’ve already talked about those games.