You can kinda start with almost any of them really, but to narrow it down a bit you'll want to look at remakes and what we often refer to as "3rd versions". Typical release pattern for Pokemon main series games has been to put out a pair of games as the first ones of a generation, then roughly a year later release a 3rd game that's basically a slightly better version of the previous pair, meaning there's little reason to get the first pair. Remakes give you a way to experience the original games if they're not available to you and are a little more up to date.
The exceptions to this are Gens 5, 6, and 8, as Gen 5 gave us a sequel pair instead of a 3rd version (and no remake game), Gen 6 never got a 3rd version or a sequel (but has a remake game), and Gen 8 seems to be replacing 3rd versions with DLC content.
So those games would be: Yellow, Crystal, Emerald, Platinum, Black/White, Black2/White2 (play Black/White before these), XY, Ultra Sun/Ultra Moon, Sword/Shield, Fire Red/Leaf Green, Heartgold/Soulsilver, and Omega Ruby/Alpha Sapphire
From there you can narrow it down further based on what gaming systems you have available and which of those games you can reasonably get (sometimes Pokemon games can be hard to find working copies of for not stupid prices), and any other things that might sway you towards any particular game.