As polarizing a leader as Donald Trump may be, there’s no denying that Time might have used one of the most unflattering pictures ever taken of the world leader. The upcoming number, titled “His Triumph,” feels oddly detached from the top-notch cover work readers have come to expect from the renowned publication. But, is it really the “Worst of all time?” As we’re about to see, Time Magazine has flirted with the idea of terrible cover photos many times before Trump’s latest pic was ever taken.
10. President Donald Trump (November 10, 2025)
Donald Trump isn’t impressed with his latest Time magazine cover. The issue, celebrating his role in the Gaza ceasefire, didn’t get his vote of confidence. “They disappeared my hair,” he complained on Truth Social. “Really weird.” Shot by Graeme Sloane, the photo sparked Trump’s latest feud.
9. O.J. Simpson (June 27, 1994)
Released during the infamous murder trial of O.J. Simpson, Time Magazine used an altered mugshot to make the disgraced celebrity look more sinister on the cover. Some saw the move as “racist” or manipulative, especially since the trial was still going on and, for all we knew at the time, O.J. might have never committed the crimes.
8. Cocktails ’85 (May 20, 1985)
Even a magazine like Time enjoys some leisure from time to time. This May cover won’t win any Pulitzers, looking more like an oversized ad for two-for-one cocktails rather than the cover of one of America’s most respected magazines.
7. Cats (December 7, 1981)
A number dedicated to celebrating our feline buddies, this 1981 cover feels like a proto internet meme. It’s certainly not one of the magazine’s most insightful journalistic jobs.
6. To the Dogs (December 12, 1994)
In 1994, Time did it again. Instead of dedicating their pages to cats, they featured dogs. This one is possibly lazier than the one for cats, featuring a sleepy canine that seems about as interested in this Time cover as any regular reader would be.
5. Fall of Japan (August 20, 1945)
Echoing the militaristic trends of the time, this cover featured Japan’s national flag (not the Imperial Rising Sun) with a black X over it, signifying the country’s defeat in WWII. The nuance that “Imperial Japan” ≠ “the Japanese people” wasn’t something American media was too concerned about at the time.
4. Is God Dead? (April 8, 1966)
This Time Magazine cover would make an excellent prop for a horror film set in the “Satanic Panic” era, but the red-on-black text-only cover appears almost too lazy by Time’s standards. Instead of inspiring theological reflection, it mostly made readers think the magazine had gone full “edgelord” decades before the internet existed.
3. Are You Mom Enough? (May 21, 2012)
One of the most bizarre Time Magazine covers ever published, “Are You Mom Enough” was immediately controversial due to its obvious attempts at manufacturing controversy for the “Mommy Wars” crowd.
2. 2020: The Worst Year Ever (December 14, 2020)
Calling 2020 the “Worst Year Ever” is a bit bold. Also bold? That big 2020 right in the middle of the Time Magazine cover. For a year that left us with so many unforgettable pictures, going to text-only mode for your big COVID-19 number was certainly a choice for Time Magazine.
1. The Surprising Joy of Virtual Reality (August 17, 2015)
Featuring the most unflattering picture of Oculus Rift’s creator, Palmer Luckey, ever taken, this picture has been the subject of constant online mockery for a decade now. Everything about it screams “awkward” to a point where we’re not sure whether Time was celebrating VR or mocking it.
RELATED: Musicians Who Died in 2025: Remembering the Legends We Lost
