A vintage photograph of a man smiling while playfully touching a woman’s hair as she looks down with a smile.
via Canva

I love a good chance to look back and appreciate how far one has come, and what better way than to do it with some yearbook photos. Does anyone else look back on their time in high school and feel like it was one big campaign? First, we had debate class, then we ran for the student council/government. From there, we competed for homecoming court or vied for the title of prom king or queen. At the end of the year, students voted on superlatives in the yearbook — you know, “most likely to succeed” and “best smile.” These vintage photos show who won those yearbook awards over the years (with some famous faces mixed in). 

1. Terry Crews and His Classmate: Most Likely to Succeed (1986)

Imgur

2. Jack Nicholson: Class Clown and Best Actor … That Checks Out (1954)

Two black-and-white yearbook photos: Left, a smiling young man and woman, with the woman giving "bunny ears" to the man. Right, the same young man kneels, holding hands with a woman as if proposing. Text lists their names and titles.
kylekujo / Reddit.com

3. Wittiest in Class (1955)

A young man sits on a stool wearing a "DUNCE" cap while holding an open book. A smiling young woman adjusts the cap on his head. Bookshelves fill the background in this vintage black-and-white photo.
UserDeleted / Reddit.com

4. Cutest Couple (1961)

Black and white yearbook photo labeled "Cutest Couple" shows Penny Holland and George Pfeil riding a tandem bicycle together on a sidewalk, both dressed nicely and looking at the camera.
brittanygeister / Reddit.com

5. Most Handsome (1964)

A black-and-white portrait of a young man in a suit and tie, resting his chin on his hand. The words “Handsome” and “Most” are arranged vertically on the left side of the image.
jste1986 / Reddit.com

6. Most Popular (1947)

A sepia-toned photo of a young man in a suit sitting on a chair, smiling. Handwritten text above reads “Popular Man 1947.” A printed caption below describes his achievements and title as Popular Man of 1947.
Imgur

7. Cutest in Class in Sarasota (1952)

Three smiling young adults sit together in a spinning amusement park ride, likely at a fairground, with tents and a sign in the background. Two women flank a man; all appear happy and excited.
mistermajik2000 / Reddit.com

8. Most Chatty (1961)

A man and a woman sit in a vintage living room, each holding a corded telephone. The woman sits on the floor, and the man sits on a couch. A record player, lamp, and framed photo are visible in the background.
scrowdy_row / Reddit.com

9. Who’s Who Senior Year (1960)

A black-and-white yearbook page from June 1960 titled "Seniors' Who's Who" features four categories: School Spirit, Quietest, Class Athletes, and Class Clowns, each with photos of students in candid poses.
thekateone / Reddit.com

10. Most Spirited Hanging Out on the Football Field (1971)

A young woman and a young man pose on a football field; the man kneels and holds a football upright while the woman stands beside him, both smiling and making peace signs. Empty bleachers are visible in the background.
dittidot / Reddit.com

11. Donald Trump Voted ‘Ladies Man’ (1963)

Black and white yearbook photo labeled "Popularity Poll" showing a young man and woman standing outside together, with the caption "Ladies' Man: TRUMP" below the image.
Imgur

12. Class Wit (1951)

A person sits on a stool in a cluttered room, smiling and wearing a large dunce cap. They are dressed in dark clothes, holding an object in one hand, with papers and books visible on shelves and tables around them.
BayRunner / Reddit.com

13. Will Ferrell Voted Best Personality (1985)

A black-and-white photo of two people standing beside a parked pickup truck, smiling at the camera, with another person sitting inside the truck. Text below reads: "Best Personality: Will Ferrell and Janet Quinn.
Mike__7 / Reddit.com

14. Bruce Willis Showing Off His Tan After Being Voted ‘Most Spirited’ (1973)

A young woman in a cheerleader outfit holding a megaphone stands next to a young man in athletic clothes in front of a wall covered with geometric artwork. Both are smiling at the camera.
UserDeleted / Reddit.com

15. Posing for the Yearbook After Being Voted ‘Class Clowns’ (Early 1950s)

Two young adults sit in old-fashioned school desks; the man is playfully holding scissors near the woman’s shoelaces while she looks down and smiles, appearing amused. A book and a box are on the desks.
mustvebeen-theroses / Reddit.com

16. Lily Gladstone: Most Likely to Win an Oscar 

Two young people stand side by side in front of an art piece. The person on the right holds a wooden mannequin. Text above reads “Most Likely To Win An Oscar,” and below are the names Lily Gladstone and Josh Ryder.
stars_doulikedem / Reddit.com

Meet the Writer

Matt has spent over the last 8 years as both a writer and editor, working in Seattle and Brooklyn, where he is now based. He loves escaping the tirelessly fast pace of the “Mad Apple” that is NYC by taking walks and runs through parks where he’s able to catch up on the latest tea about society from the city’s ever chatty, always hungry, occasionally maniacal, pigeons. They always have a lot to say. When he’s not taking his urban nature strolls, or dutifully combing the deepest rabbit holes of the internet to find the content that’s worth sinking your mind’s teeth into, he’s likely holed up at a dark-lit dive bar with a new book and/or some friends, or just easily he could be on the hunt for the next addition to his steadily growing plant family.