15 Boss-Level Celebrities that would make Awesome Chauffeurs

‘Boss’ Defined – “Incredibly Awesome; miraculous; great” – From urbandictionary.com

After researching “How to Be ‘Like a Boss’” for several hours, I have compiled the following criteria for this list of Boss Celebrity Chauffeurs. Now of course, this is entirely subjective, but I will say that I do think that after only mere hours, I have a high degree of authority on the subject matter.

Sadly, I must admit to you all, I cannot call myself a Boss.

Before we get started, please feel free to tune into any of the following “Boss” Playlists. Just to get you in the mindset of one. It’ll make the whole “driving experience” that much better.


Boss Criteria

What better way than to create a wicked cool acrostic


Brawls never expected or started, but they’ll take anyone down if need be

Oozes confidence but never arrogance

Strikes down all obstacles: Dinosaurs, villains, ghosts – or in real life: Famine, disease, bullies

Smiles in the face of danger – They are a force to be reckoned with


1. Will Smith a.k.a.  Boss of Bel Air

Will Smith

I am pretty sure Will Smith was born a Boss. Even as a young actor in Fresh Prince of Bel Air, he proved this. I’d trust him driving me around town, especially when that alien invasion happens.

Not only did he save the world from an alien attack, he himself survived an Internet Death. That’s right, on March 16th, 2015, rumors flooded Facebook telling the world Will Smith had fallen 60 feet while filming in New Zealand. Not quite the case obviously being that he is alive and well and turned out to be one of many death hoaxes. But if these types of rumors are being made about him, you gotta know that he’s reached the legendary status of Boss.

Trust me if anyone were to cut him off, he would be right there mouthing to the other driver, “Awe Hell No!”


2. Betty White a.k.a. The Golden Boss

Betty White

Betty White will make sure all fellow drivers know who’s boss — and that’s her of course. She’s probably been driving the longest out of any of the other celebrities on this list. Also among one of the victims of the Internet Death Hoax, she has proven herself worthy of the title: Betty the Golden Boss.

Plus, check out her wicked cool shades. She’s pretty much taking Boss to a whole other level


3. Harrison Ford a.k.a. the Prodigal Boss

Harrison Ford

When Harrison Ford was born – the world shook – for the Prodigal Boss had arrived.

Even as a little lad it was clear that not only was Harrison Ford destined to be some of the most iconic movie characters out there, he would prove himself to be a renowned Boss.

Seriously, guys…

HE LANDED A PLANE. He’s Han Solo AND Indiana Jones. Need I say more?

A ride with him would be an adventure!


4. Oprah Winfrey a.k.a. The Bonafide Boss

Oprah Winfrey

I don’t think any number of words can embody Oprah’s Boss-ness. She has done more in her life than one can even fathom.

She might actually be one of the most expensive chauffeurs out there, but it’d probably be worth it. She might just give you the car. She is infamous for it… Like a Boss!


5. Ryan Gosling a.k.a. The Late Blooming Boss

Ryan Gosling

It wouldn’t be right not include at least a few Canadian celebs in here. Gosling definitely fits the Boss criteria, especially after his starring role in Drive. A bit of a late blooming Boss I’d say. .

We all know the #1 Rule of driving is to have 100% confidence in yourself. And I would say his air of confidence is up there. He quite literally oozes Boss confidence. I mean who wouldn’t be confident with Eva Mendez at your side. Who is a Boss in her own right.


6. Bruce Willis a.k.a. The Heavy Weight Champion Boss

Bruce Willis

Looks like your phone just entered into its roaming mode. Why you ask? Well you’ve just entered “The Willis Zone”.

He takes the cake when it comes to being a Boss.. If any other of these Boss celebrities were to enter the ring with Willis, he’d pretty much own them by the end of it. Which is why he is most definitely the Heavy Weight Champion Boss.

Pretty sure he can save anyone, from anything, anywhere, in any area code, at any point in time – past, present or future. What better person to drive you around. I bet he’ll probably tell you a story.


7. Angelina Jolie a.k.a. Queen Boss

Angelina Jolie

Laura Croft was her first step into the life of a boss… From there, she continued to take    on roles, each helping her down the path, until one day…. She was dubbed Queen     Boss.

Not only does she attempt to make the world a better place, one adopted child at a time. (But seriously, she has made a real difference in the lives of thousands of children.) She really tries to remain out of the lime light, making her all the more mysterious which is another reason to deem her a real Boss.


8. Christopher Lee a.k.a. Lord Boss

Christopher Lee

Okay first and foremost, his stare will make anyone scared to cut him off. So that’s a bonus. Second, have you seen Lord of the Rings? I would not want to mess with this guy when he gets in a mood. Road rage might just end up with you being seriously mangled.

I would be weary of being a back seat driver though.


9. Gabriel Macht a.k.a. The Boss Closer

Gabriel Macht

By now, we should have probably all watched Suits. If not, then I would suggest watching it immediately after reading this blog post.. . Well then you also know Harvey Specter. Just in case you don’t… Here is a clip of his Boss bravado.

Video — https://www.youtube.com/watch?v=J0i95LgcxIc

I can only imagine that this sort of attitude would make him quite the chauffeur. He won’t take crap from any one on the road. And if you were ever to get into an accident, he’d probable talk his way out of it for you. He is the #1 closer after all.


10. Kiefer Sutherland a.k.a. The  Boss in Shining Armor

Kiefer Sutherland

Just when you thought Sutherland couldn’t get any cooler. This happened:

Brook Shields was knocked down by fashionista Jack McCullough. So, like any Boss would, “Sutherland demanded McCullough apologize. McCullough pushed Sutherland, and the actor responded with a head-butt” TVGuide.com

This guy can save the world in 24 hours, multiple times. You want him behind the wheel.


11. Scarlett Johansson a.k.a. The Killer Boss

Scarlett Johansson

Not only has she played some of the most epic characters is countless films; she has recently been immortalized by a hilarious, albeit creepy surprise kiss from iconic actor John Travolta. Careful John, she might be poisonous – she is, after all, the Black Widow.

Johansson would make a seriously legit chauffeur.  With her countless action films, she definitely has some stunts to get you to where you need to be. Perhaps with her super brain she could split the sea of traffic.


12. Gordon Ramsay a.k.a. Master Boss

Gordon Ramsay

As a chauffeur Gordon Ramsay would destroy anyone in his way. I don’t even think you would know what to do if you got into a confrontation with this guy. Master Chef of the kitchen combined with his Boss behavior makes him Master Boss.

That smirk is only a front. In reality if anyone makes a mistake while driving you around, at least you know he won’t stand for it. Well worth having, especially in New York or LA where it seems like drivers act like Honey Badgers.


13. Robert Downey Jr a.k.a. The Legendary Boss

Robert Downey Jr

Oh yes, the legendary Boss Robert Downey Jr would make a marvelous chauffeur.

Urban Dictionary Definition of Robert Downey Jr:

“One of the most talented, versatile and admirable (not to mention badass) actors of our time. Has persistently displayed witty performances alongside depth and variation throughout his impressive career”

He is even defined as badass (another word for ‘boss’). He is for real.

If he doesn’t drive you, he’ll probably just fly you around as Iron Man.


14. Liam Neeson a.k.a. The Boss Jedi

Liam Neeson

Crap, there goes a wheel. Pftttt. Liam Neeson doesn’t need it. He’s a driving Jedi. Taken 1, Taken 2, and now Taken 3. Each movie takes him one boss-level higher.

You could expect nothing but the best chauffeuring from Neeson. He demands respect after all. What with that epic accent. I wouldn’t want to upset this guy while driving.


15.  Morgan Freeman a.k.a. The Original Boss

Morgan Freeman

How many voice overs do you think this man has done? My bet is over 20 for sure.

I mean his voice alone gives him Boss cred. I think that not only would he be an excellent chauffeur, but that all Siri voices should be altered to sound exactly like him.

Perhaps his next big movie could be called “HIM”?

Funny enough, looking back on this list, it seems like there are 3 Avenger actors. Perhaps this might have to become a requirement of Boss Criteria? Makes sense… I mean The Avenger movies are Boss themselves.


Any other Avengers you think should be a part of the list?