Oh, damn. Hard to choose, man. Even his worst album (Figure 8) has some quality tracks on it. Just give the songs I mentioned a listen.
Other ones to listen to include The Biggest Lie, Coast To Coast, Alameda, Independence Day, A Distorted Reality Is Now A Necessity To Be Free, Baby Britain, Ballad of Big Nothing, Can't Make A Sound, Either/Or, Going Nowhere, No Confidence Man, Roman Candle, St. Ides Heaven, and Suicide Machine.
You really can't go wrong with any song of his, though. My absolute favorite singer/songwriter ever.
Rose Parade, A Fond Farewell, Son of Sam, Waltz #2, Junk Bond Trader, Angeles, Miss Misery, King's Crossing, Needle In The Hay, Say Yes, Sweet Adeline, Between the Bars, Let's Get Lost, Pictures of Me, Happiness - I could name fantastic songs he's recorded all day long.
I like pretty much everything he ever recorded, even earlier sh*t with Heatmiser.
Check out his other albums if you haven't already, though. Smith was, in my opinion, the greatest loss for the world of music since John Lennon - An absolutely brilliant singer/songwriter who every fan of music should give a listen to.