Scottish photographer Harry Benson has photographed every U.S. president since Dwight D. Eisenhower. And he also documented Donald Trump more than any other photographer throughout the last 40 years, memorably capturing the President-elect holding a million dollars cash at the Trump Taj Mahal in Atlantic City in 1990. Two years ago, while photographing the millionaire-mogul, Benson had a suggestion for Trump: “You should run for President.”
In the spirit of tradition, TIME reunited the duo for a photo shoot appearing in the July 25 issue, and when Trump walked into the room it was the first thing Benson mentioned. The resulting portrait, Trump seated at his desk with hands extended in his trademark gesture, is one of the best portraits TIME commissioned this year and showcases in this gallery as 2016 comes to a close.
The subjects of our best portraits include artists like Lin-Manuel Miranda, politicians like Dilma Rousseff, athletes such as Simone Biles and the headline-making Fox News commentators Megyn Kelly and Gretchen Carlson. These are just a few of many more influential leaders in politics, entertainment, business, sciences and the arts we photographed over the last 12 months. Plus there are the unknown people from the recipient of the most extensive face transplant ever to the families of EgyptAir passengers lost on Flight 804.
In this chronological gallery, TIME’s photo department presents its selection of the best portraits it commissioned in 2016.