10 Unlikely CEOs Who Would Run a Company Like a Boss (Some Might Surprise You!)

When you think of a successful CEO, you probably picture a smooth-talking, suit-wearing corporate juggernaut—someone with a LinkedIn profile packed with buzzwords like "synergy," "disruption," and "thought leadership." But what if we told you that some of the most unlikely candidates could also run a company… and run it well?

From historical conquerors to fictional oddballs, we’ve ranked the Top 10 Unlikely CEOs based on leadership, strategic thinking, and, let’s be honest, sheer entertainment value.

1. Caesar 9/10 (Planet of the Apes)

Could Caesar from Planet of the Apes Succeed as a CEO? Leadership Lessons from the Alpha Primate

Could Caesar from Planet of the Apes run a Fortune 500 company? We break down his experience, communication skills, and crisis management to see if he’s corporate material or just monkey business.

Office BantomimeJames Mason

If you're looking for a CEO who can unite factions, drive innovation (or at least survival), and lead with both intellect and strength, look no further than Caesar. He transformed an oppressed species into a formidable force—something many business leaders would envy. If he can organize a revolution, handling a boardroom of middle managers should be a breeze.

2. Dorothy 8/10 (The Wizard of Oz)

Could Dorothy Gale From The Wizard Of Oz Pull It Off As A CEO

Could Dorothy from The Wizard of Oz swap her ruby slippers for a corner office? We assess her CEO potential by ranking her skills—humour included. Is she corporate material? Let’s find out!

Office BantomimeJames Mason

Dorothy’s resume? She built a strong, diverse team (a heartless robot, a spineless feline, and a brainless scarecrow), kept them motivated despite setbacks, and successfully overthrew a dictator. Plus, she navigated corporate politics (a.k.a. the Wizard’s deception) and still made it home on time. Strong leadership, and excellent delegation—Dorothy’s got CEO material written all over her.

3. Alexander The Great 7.6/10

Could Alexander the Great Survive as a Modern CEO?

Alexander the Great conquered nations, but could he conquer a corporate boardroom? This humorous breakdown of his traits ranks his CEO potential from communication to crisis management.

Office BantomimeJames Mason

One of history’s most ambitious leaders, Alexander expanded his empire faster than any modern startup. He had a vision, adaptability, and an unrivalled ability to conquer new markets (literally). But his tendency to burn out employees (or, you know, entire civilizations) might make investors a little nervous.

4. Mary Poppins 7.5/10

Could Mary Poppins Thrive As CEO? Unpacking Her Leadership Magic

Could Mary Poppins step out of her magical carpet bag and into the boardroom? We rank her CEO-worthy traits with humor and insights to answer the question: Is she “practically perfect” for the job?

Office BantomimeJames Mason

She arrives unexpectedly, fixes everything, and leaves without asking for credit. Mary Poppins is the ultimate transformational leader. With an ability to inspire even the most hopeless workforce (or children), she’d likely turn any struggling company into an industry leader. Plus, she gets bonus points for a strong commitment to work-life balance—who else can teach efficiency with a spoonful of sugar?

5. Napoleon Bonaparte 7.2/10

Could Napoleon Bonaparte Be the Ultimate CEO? Ranking His Leadership Skills

Could Napoleon Bonaparte conquer the workplace like he did Europe? We ranked his CEO traits—communication, empathy, crisis management, and more—in a playful deep dive into history and leadership.

Office BantomimeJames Mason

The original “move fast and break things” leader, Napoleon was bold, decisive, and relentless in his expansion plans. Sure, he had a bit of an ego, but plenty of modern CEOs do. His biggest downfall? A tendency to overextend. If only he had a solid risk management department, Waterloo might have been a different story.

6. Hans Gruber 7/10 (Die Hard)

Hans Gruber As A CEO, Could He Have Pulled It Off?

Could Hans Gruber from Die Hard have been a successful CEO? With his strategic thinking, charisma, and ruthless risk-taking, he’d fit right in—if you overlook the minor issues of ethics and explosives!

Office BantomimeJames Mason

Let’s be clear—Hans Gruber is a villain, but that doesn’t mean he lacks CEO potential. He’s calculated, strategic, and knows how to execute (his plans, that is). His biggest mistake? Underestimating a lone cowboy-style employee who refused to follow corporate policies. If not for John McClane, Nakatomi Tower would have been his.

7. Ebeneezer Scrooge 7/10

From Miser to Manager: Would Scrooge Make a Great CEO?

Ebenezer Scrooge, the infamously grumpy miser from Charles Dicken’s famous novel, A Christmas Carol, as a CEO? Let’s rate his leadership traits with a twist of humour and find out if he could thrive in the corner office!

Office BantomimeJames Mason

A classic turnaround story. Initially, Scrooge would have been the worst CEO imaginable—cutting costs, underpaying staff, and cancelling Christmas bonuses. But after a bit of "mentorship" from the supernatural consulting firm of Past, Present & Future, he transformed into the kind of leader employees would love. Proof that even the worst corporate overlord can be redeemed.

8 Clark Griswold 6/10 (National Lampoon’s Vacation)

Clark Griswold as CEO: How Would He Fare in the Corporate World?

Could Clark Griswold’s with his over-the-top hilarious antics send him down the road to success as a CEO? Let’s rank his leadership qualities like communication, risk-taking, and crisis management—spoiler alert: ″I got a bad feeling about this!″

Office BantomimeThe Office Bantomime Team

A CEO full of big ideas, Clark has vision and ambition but lacks execution. He’s the kind of leader who starts a risky new initiative (“Let’s surprise the family with an unplanned road trip!”) without proper planning, then wonders why it all falls apart. However, his ability to keep morale high despite total chaos is commendable.

9 Willy Wonka 5.4/10

From Chocolate Factory to Boardroom: Is Willy Wonka Fit to Be CEO?

Could Willy Wonka thrive as a CEO? From his eccentric leadership style to his risky decisions, we break down his skills (or lack thereof) in a hilarious review.

Office BantomimeJames Mason

Creativity? Check. Innovation? Check. Ethical workplace? Uh… not so much. Wonka might have brilliant ideas, but his employee turnover rate (or rather, employee “disappearance” rate) would be a nightmare for HR. Also, there’s the issue of safety violations—an entire factory with zero guardrails? A lawsuit waiting to happen.

10 Alan Partridge 5/10

Could Alan Partridge Be CEO Material? A Dive Into His Leadership Skills

Could Alan Partridge handle the CEO chair? From his “experience” to “crisis management,” Let’s evaluate his corporate potential. Spoiler: It’s a rollercoaster ride or more so, a Lexus IS which is Alan’s preferred car.

Office BantomimeJames Mason

If charisma alone could run a company, Alan Partridge would be a Fortune 500 CEO. Unfortunately, a CEO also needs self-awareness, decision-making skills, and the ability to read the room—three things Alan is terribly lacking. That said, he’d make a killer motivational speaker for an annual sales conference.

Final Thoughts

While some of these figures might not thrive in today’s corporate landscape (looking at you, Wonka), others could absolutely give today’s CEOs a run for their money. Caesar, Dorothy, and even Mary Poppins showcase leadership qualities that modern executives should take notes from.

Who do you think would make the best (or worst) CEO? Let us know in the comments!