To make a valid block, you have to start with another valid block. The difficulty is set (edit: I was wrong, and I fixed this) every 2016 blocks based on how long they took to mine. This works out to about 2 weeks at the expected rate of mining. The average time of those 2016 blocks is then used to calculate the difficulty of the next 2016 blocks, and the difficulty is marked down in the chain itself.

So in your hypothetical you’d have to solve around two weeks worth of blocks at the current difficulty level, which isn’t possible in a human lifespan. After that the difficulty for your chain would rapidly fall, but your sub-chain would already be very far behind and would never catch up.

I’ve always assumed that the notion of longest chain takes difficulty into account, although I haven’t really been able to find confirmation of this.