Cross Country Fun: 14 Famous People Who Would Make the Perfect Road Trip Buddy

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Road trips can be a lot of fun, especially if you have the right passenger to navigate, play DJ, and share snacks with. This idea got me thinking–who would be the best famous person to drive cross country with?

That would depend on what kind of trip you want to experience. Are we talking about hitting the weird, off-the-beaten-path dive bars and eateries, or do you want to have long philosophical conversations about the world, historical and current events?

But why limit ourselves? Let’s have the best of both worlds with these 13 famous personalities who are just the right mix for a leisurely, unpredictable journey. 

1. Keanu Reeves

Imagine cruising up and down the Hawaiian coast with actor Keanu Reeves in a Jeep with the top down, wind in your hair, and music blasting. Your conversation would stretch from his John Wick character, and you would share how you would go on a revenge spree if someone messed with your dog to when is the best time to catch a wave around Oahu.

Of course, you would have to stop at a random food truck, grab a delicious bite to eat, and proceed to make someone’s day by buying them lunch because that’s just how Keanu rolls.

2. Dolly Parton

The queen of country, Dolly Parton, would make an exceptional cross-country road trip buddy. She would pull out her rhinestone-studded guitar and write a hit tune about the crazy adventures the two of you had along the way.

I can hear her sweet, sassy voice and charming giggle as you stop by Graceland and then make your way to the Rocky Mountains. She would regale you with stories of growing up impoverished in the Appalachians and how important it is for her to fund literacy programs. 

3. Barack Obama

Former president Barack Obama would be the perfect companion on any road trip. Why? First, he has excellent taste in music, so his DJ skills would be top-notch. Secondly, he would be cracking jokes about your driving skills the whole time. Thirdly, you would have the privilege of riding in the car with the first Black President of the United States.

The wealth of knowledge about the world and current events would be a master class like none other. 

4. Martha Stewart & Snoop Dog

Can you imagine taking a trip with the infamous duo “Queen of Decor” Martha Stewart and rap legend Snoop Dog? Hands down, that trip would include the best snacks, specifically brownies and tunes.

It would be incredible to be a fly on the wall with these two cracking jokes, telling stories about jail and what makes the best mac and cheese. You would get to experience it all while driving and checking out the views the US offers. 

5. Madonna

Madonna has seen and done it all throughout her decades-long career in show business. Taking a road trip with her as your companion would be epic. She would share stories about making a name for herself as a young woman on the streets of NYC, her iconic movie and music successes, and her philanthropic endeavors throughout the years.

And let’s not forget the countless costume changes she will make at rest stops. The Queen of Pop will only ride in glorious style.

6. Pedro Pascal

Pedro Pascal is so hot right now, and I don’t just mean looks. Although, he does make for excellent eye candy. Pascal has risen to fame from his start on Game of Thrones to the Mandolorian and most recently as the star of The Last of Us.

However, this isn’t why he would make a great road trip buddy. He genuinely comes across as a nice guy who could carry on a great conversation on various topics, and he would undoubtedly fit in at any dive bar you decide to stop at. 

7. Mark Hammil

The one and only Luke Skywalker would bring the antics and all his Jedi wisdom with him on a cross-country adventure, making Mark Hammil the perfect co-pilot.

You would never get lost in the middle of nowhere because he would come prepared with already downloaded directions if you lose the Wi-Fi signal, and you would get a first-hand account of behind-the-scenes stories while filming Star Wars—a complete win/win.

8. Stevie Nicks

Stevie Nicks, the front woman of the iconic 1970s band Fleetwood Mac, would be another ideal candidate for an unforgettable road trip. Just imagine the stories and scandals she would share along the way.

You might be the lucky recipient of all the juicy gossip surrounding her, Lindsey Buckingham, the other bandmates, and what ultimately led to all the betrayal and subsequent breakup of the band. 

9. Nicolas Cage

Nicolas Cage is a known weirdo, which would make him an excellent choice to road trip with. Your adventure will occur somewhere in the Deep South and end up in New Orleans, where he has been a resident for many years.

Along the way, you will get into crazy conversations about his film work, marriages, and the myriad other stories he undoubtedly has up his sleeve. 

10. MVP Kamala Harris

She might not be everyone’s first choice as a traveling companion, but she is undoubtedly on my shortlist. The reason? She is the first woman of color elected to the Vice Presidency of the United States. How she has achieved so much is worthy of a long, detailed conversation.

To be able to pick her brain and learn so many intricate details of helping to run a city, a state, and now a country is a moment that would leave an indelible impression.

11. Stephen King

The King of Horror has to be on this list, and it would be a fantastic trip filled with visits to the creepiest, abandoned locations ever. Together, you would devise and pen the next best-selling horror novel. Along the way, he would share what inspired his other classic books and why horror is his favorite genre to write.

However, I also like to believe he would go on some incredible political rants that would leave you in stitches from cry-laughing so hard, as evidenced by his Twitter account.  

12. Jack Black

Jack Black would be another fantastic road trip companion. The music, jokes, and snacks he would dole out would be epic proportions. There would be no shortage of laughs while he performed car karaoke, doing his best Britney Spears impersonation and Tenacious-D renditions.

Undoubtedly, Black would always be willing to stop at the most ridiculous places, like the largest rocking chair or giant ball of yarn, to capture the perfect Instagram picture. 

13. Dan Rather

There would be no shortage of information, incredible stories of first-hand accounts of historical events, and wisdom departed by retired journalist Dan Rather. As a young reporter, Rather delivered news of the Vietnam War, John F. Kennedy’s assassination, and the Watergate investigation.

His knowledge of those three world-changing events alone would be enough to make me want to travel across the US with him as my co-pilot.