I usually go for particular albums, and some of my favorite ones are 3rd by Big Star, In the Wee Small Hours by Frank Sinatra, Violent Femmes' self-titled album, Pinkerton by Weezer, Pet Sounds by The Beach Boys, most anything by Simon & Garfunkel, and Let It Be by The Replacements. That should get you started.
The Ultimate Heartache Playlist
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