Here are some of my favorites, in no particular order.
"Screw Mastery" in Lenny Letter, about the humiliation and pleasure of switching careers in your 40's - in my case, going from writing to radio.
"Murder by Craigslist" in the Atlantic, about a man who lured several men to a farm through a Craiglist ad and then killed them, and the surprising thing these gruesome murders reveal about America.
"A Boy's Life," in the Atlantic, about a very young boy in a rural conservative town who is sure he is a girl. This story was early to explore the serious complications of transitioning so young.
"The Overprotected Kid," in the Atlantic, where I puzzle on why I was raised so differently than how I am raising my children, and what we've lost by being so preoccupied with safety.
"The Silicon Valley Suicides," in the Atlantic. An overprotected kid part 2. The problem with our preoccupation with optimizing our children.
"The Case Against Breastfeeding," in the Atlantic. An angry but reasoned (and scientific!) critique of our obsession with breastfeeding. Very controversial at the time but every year I get a dozen notes of gratitude from new mothers who couldn't or didn't want to breastfeed.
"Hello, My Name is Stephen Glass, and I'm Sorry," in The New Republic. In 1998 I - and the rest of the world - discovered that my good friend and colleague Stephen Glass had made up many of his stories. In this story I go visit Steve and try and answer the question: how do you know if someone has really changed?
All my Atlantic stories.
All my Slate stories.