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A lot’s changed in this city since we launched nearly 20 years ago—back then, New York neighborhoods were known for their grit rather than their coffeeshops, affordable apartments were actually a thing, and legend has it that the L train actually kinda worked. Throughout all that tumultuous change, Time Out New York has steadfastly put out a magazine every week showing New Yorkers the absolute best of everything the city has to offer. To celebrate the milestone, we’re looking back at 50 of our covers, some stunning, some funny, some…well, some where we’re just not entirely sure what we were thinking (Kevin Costner’s face on a Christmas tree ornament, we’re looking at you). We’ll let you be the judge of which ones have stood the test of time.