Tons of great value pins ($1500 and below) that won't wreck your wallet.

Bally/Williams (pre DMD): Black Knight, Black Knight 2000, Elvira and the Party Monsters, High Speed, Pinbot, Space Shuttle, The Machine: Bride of Pinbot

Bally/Williams (DMD): Dr Who, Party Zone, Terminator 2, High Speed II: The Getaway, Bram Stoker's Dracula, Demolition Man, Judge Dredd, Johnny Mnemonic, No Fear, and NBA Fastbreak. Indianapolis 500 is another kick-butt pin, but its kinda hard finding one nowadays. I think the best bang for your buck for this era, as far as Bally/Williams goes, I'd cast my vote to The Shadow (disgustingly addictive due to the difficulty with almost perfect software).

Data East: Last Action Hero, Jurassic Park, Tales from the Crypt

Sega: Batman Forever, Goldeneye, Mary Shelly's Frankentein, Starship Troopers

I want to add Data East's Tommy, but like gweepose found out....the price on Tommy machines seems to go up. Good thing about finding a Tommy, is they are usually in good shape (the ones I have seen anyway). If anything, the machine might be missing the sweet pinball topper, but thats about it.

I also wanted to add White Water, but this one seems to push past the $2000 price tag nowadays. Be it nostalgia or people hyping it up....the thing seems to be climbing up in value.

PS: Great choice of adding Dirty Harry gweempose! A great pin vastly underappreciated, ESPECIALLY for how much you can pay for one. Super cheap late Williams DCS pin, and for the most part, are in great condition when you find one (near flawless playfields with little cabinet fade...maybe a finnicky gun).