1

122 S. Michigan Ave.

Image: Allen Boguslavsky

Why not start the trip at the place where it all began? For Route 66, the beginning is right in the heart of Chicago , at 122 S. Michigan Ave. Look for the iconic pylon near the intersection of South Michigan Avenue and East Adams Street.

Fun fact: the Mother Road didn’t always start there. Back in 1926, Jackson Boulevard at Michigan Avenue was the official launch point for travelers!

2

Gateway Arch

Image: Intricate Explorer

Follow your adventure in St. Louis with the Gateway Arch, a towering 630-foot tribute to westward expansion. This stainless-steel beauty isn’t just a landmark, it’s an experience in itself.

Ride the tram to the top for jaw-dropping views of the Mississippi River and the city skyline. It’s the perfect way to set the tone for the rest of your journey.

3

Route 66 Drive-In Theater

Image: Tim Mossholder

Ready for some vintage vibes? Swing by the Route 66 Drive-In Theater in Carthage, Missouri. This blast from the past offers double features under the stars , just like in the good old days.

Opened in 1949, closed in 1985, and re-opened in 1998, this drive-in theatre has functioned ever since and plays two movies from Friday to Sunday every single week. Bring your lawn chairs and a cooler, or cozy up in your car for the full retro experience.

4

The Golden Driller

Image: Jametlene Reskp

Now it’s time to meet the Golden Driller, a 76-foot-tall oil worker who’s been standing proud in Tulsa, Oklahoma, since the 1960s.

It’s one of the largest freestanding statues in the country and a nod to Oklahoma’s rich oil history. At the base, there’s a sign that reads: "The Golden Driller, a symbol of the International Petroleum Exposition. Dedicated to the men of the petroleum industry who, by their vision and daring, have created from God’s abundance a better life for mankind." Strike a pose with this gentle giant, and you’ll feel downright tiny.

5

Route 66 Museum

Image: Carol Highsmith's America

For the following stop, you can take a break to explore the Oklahoma Route 66 Museum in Clinton. In it, you’ll be able to see artifacts, photos, and exhibits celebrating the history of the Mother Road.

Wander through rooms themed by decade, and you’ll feel like you’re traveling through time. From the Dust Bowl to the heyday of diners, this museum paints quite a vivid picture of Route 66’s golden era. And, of course, you can go by the gift shop to get a road trip memento.

6

Cadillac Ranch

Image: Heidi Kaden

If you’ve ever wanted to graffiti a Cadillac, this is your chance. Cadillac Ranch in Amarillo, Texas, features 10 half-buried cars sticking nose-first out of the ground. It’s an open-air art installation that’s as weird as it is wonderful.

Grab a can of spray paint (provided by friendly locals or your fellow travelers) and leave your mark. Just be warned, it might only last a day before someone else paints over it!

7

Route 66 Halfway Point

Image: Vicky McLain

Welcome to Adrian, Texas, the official halfway point of Route 66! You’re 1,139 miles from both Chicago and Los Angeles, so take a breath and celebrate!

The MidPoint Café is famous for its "ugly crust" pies. Don’t trust the name; they are actually delicious! It’s a perfect pit stop to recharge and think about the fact that you’ve conquered half of the Mother Road. Only halfway to go!

8

Meteor Crater

Image: John Ballem - a collection of personal photos

Arizona is home to some magical attractions, and Meteor Crater is no exception. This massive impact site, located near Meteor City, was created by a meteorite over 50,000 years ago . Standing on the rim and peering into the 560-foot-deep crater, you’ll feel like a tiny speck in the universe. The visitor center has some cool exhibits on space and meteors, which is perfect for science lovers or anyone who likes their roadside stops with a side of awe.

9

Old Trails Bridge

Image: Jimmy Whitson

Crossing the Colorado River into Arizona, the Old Trails Bridge in Topock is a picturesque reminder of Route 66’s early days. Though it’s no longer open to traffic , it’s a popular photo spot for travelers.

The rusted steel beams and sweeping desert views will give you a beautiful moment. Pause here, take in the history, and imagine the countless cars that once went across its span.

10

Burger Hut

Image: Haseeb Jamil

Needless, California, may be small, but it’s big on charm, especially at Burger Hut. This unassuming little eatery is beloved for its old-school burgers, fries, and milkshakes. It’s the kind of place where the food is made with love , and the portions are hearty. Don’t take our word for it; just go try it!

After hours on the road, there’s nothing better than a juicy burger and a chance to stretch your legs. This spot is a gem along Route 66!

11

Hollywood sign

Image: Scott Greer

As you approach the end of Route 66, why not take a detour to see the world-famous Hollywood Sign? Perched on the hills overlooking Los Angeles, it’s a symbol of dreams and stardom .

Take a hike to the best viewpoints for some exercise (and epic photos, of course). Sure, it’s a bit off the beaten path, but what’s a road trip without a side quest?

12

Santa Monica Pier

Image: Joel Mott

You’ve made it! The Santa Monica Pier marks the official end of Route 66 . With its iconic Ferris wheel, arcade games, and ocean views, it’s the perfect spot to celebrate completing your journey.

Now you’re done, dip your toes in the Pacific, grab a cone of soft-serve, and reflect on all the memories you’ve made along the way. The Mother Road may end here, but the stories you’ve collected will last a lifetime.

1

Robert De Niro vs Mickey Rourke

Image: Vitruvian Badr

At first glance, it was the typical 1980s film set. But when Robert De Niro and Mickey Rourke worked together in Angel Heart , their differences in style weren’t just noticeable; they were combustible. De Niro, famous for disappearing into his roles with a strict Method approach, didn’t always mesh well with Rourke’s more unpredictable, improvisational take.

According to lore, all hell broke loose when Rourke decided to ignore De Niro’s suggestions for a scene. What was supposed to be a straightforward shoot turned into multiple takes, frustrating not just the two stars but the entire crew. The altercation quickly became Hollywood gossip, with insiders saying it was a classic case of two strong personalities refusing to give in.

2

David Letterman vs Jay Leno

Image: John-Mark Smith

Who deserved the late-night crown , Letterman or Leno? For years, Americans were unable to settle the debate. On screen, both comedians exchanged polite words and even jokes, but behind the curtain, the situation was a little more complicated.

Reporters loved to stir the pot, writing headline after headline about which funnyman truly deserved the throne. Viewers, meanwhile, treated it almost like a sporting match, tuning in to see who would come out on top. In truth, much of the "feud" was blown out of proportion, yet the friendly jabs and constant comparisons managed to keep audiences entertained.

3

Dean Martin vs Jerry Lewis

Image: anncapictures

On stage, there were only gags, music, and applause. But behind the scenes, Dean Martin and Jerry Lewis were falling apart. Martin often felt stuck playing the calm, serious foil while Lewis stole all the laughs with his wild, over-the-top routines.

Over time, that imbalance created real tension. After starring in 16 hit films together, the famous duo finally called it quits. Their split was so final that they didn’t exchange a word for two full decades. Fans were stunned when they eventually patched things up later in life, a reminder that even the biggest comedy legends aren’t immune to bruised egos and long silences.

4

Olivia de Havilland vs Joan Fontaine

Image: cottonbro studio

Few family feuds reached the heights of Olivia de Havilland and Joan Fontaine’s legendary rivalry. The sisters were competitive long before the bright lights of Hollywood, each vying for their mother’s attention. Once both became movie stars, the bad blood only grew stronger.

In 1942, the two actresses were even nominated for Academy Awards in the same category. Fontaine ended up winning and later claimed her older sister pulled her hair during the ceremony. That incident became one of Hollywood’s most talked-about snubs. Their quarrel stretched on for decades, marked by jealousy, pride, and the kind of family drama that the public can’t get enough of.

5

Elton John vs Madonna

Image: HubertPhotographer

It may sound like sensational news, but Elton John once declared Madonna’s Bond theme "the worst ever." From that point on, the two megastars exchanged sharp words through the press, with Elton poking fun at her performances and Madonna brushing off the criticism with icy charm.

Reporters loved every jab, turning their spat into tabloid gold. Though they occasionally patched things up, the rivalry lingered. Even music royalty can squabble just like the rest of us!

6

Marilyn Monroe vs Jayne Mansfield

Image: WikiImages

In the 1950s, Hollywood had room for only so many platinum blondes, and Marilyn Monroe was already the reigning queen. When Jayne Mansfield came to light with her hourglass figure and playful charm, the press quickly dubbed her "the next Monroe."

Marilyn, who guarded her image carefully, bristled at the idea of a copycat stealing her thunder. Meanwhile, Mansfield leaned into the comparisons, showing up at events in daring outfits and orchestrating photo ops that guaranteed headlines. The result was a highly public rivalry that fascinated fans, turning every red carpet into a showdown.

7

Johnny Carson vs Joan Rivers

Image: Debby Hudson

One phone call never answered, one friendship lost forever. Joan Rivers owed much of her early success to Johnny Carson, who gave her a career-changing boost as a regular guest on The Tonight Show . For years, she was seen as his comic protégé, someone he personally championed. But when Rivers accepted an offer to host her own late-night program, Carson viewed it as a betrayal.

He cut off contact immediately, refusing to take her calls, and the friendship that once seemed unbreakable collapsed overnight. Fans were stunned to see the bitter end of what had appeared to be a classic mentor-and-student bond. The silence lasted all their lives.

8

Debbie Reynolds vs Gene Kelly

Image: Kazuo ota

When Debbie Reynolds starred in Singin’ in the Rain , she was a 19-year-old performer stepping into a major role for the first time. Gene Kelly, already an established star, demanded flawless performances and wasn’t known for his patience. Reynolds later recalled long hours of grueling rehearsals, where Kelly frequently criticized her every move, reducing her to tears.

Though their discord was rooted more in his high standards than personal dislike, the experience marked a harsh introduction to Hollywood for the young actress. Today, their behind-the-scenes tension is remembered as both a glimpse into Kelly’s tough reputation and a reminder of the enormous pressures that came with working alongside legends.

9

Orson Welles vs William Randolph Hearst

Image: William Warby

When Citizen Kane hit the screens, it wasn’t just a film debut; it was the spark of one of Hollywood’s fiercest battles. William Randolph Hearst, the media tycoon who saw too much of himself in the story, launched an all-out war against Orson Welles.

He tried to bury the film before it could reach audiences, banning ads in his papers and fueling smear campaigns. What began as a clash of egos grew into a cultural showdown, forever linking their names to both scandal and cinematic history.

10

Frank Sinatra vs Marlon Brando

Image: Brett Sayles

If you watch Guys and Dolls today, all you’ll see is glamour. In reality, the shooting was pretty stressful: Sinatra craved efficiency, Brando thrived on slow-burning performance. Brando’s Method acting tested Sinatra’s patience, as Ol’ Blue Eyes favored efficiency and clean, polished takes.

Rumors of heated exchanges and icy silences hit the media, and by the final days of filming, the pair were barely speaking. What should have been a classy production became notorious for its behind-the-scenes tension, adding an extra layer of drama to the musical classic.

11

Bette Davis vs Joan Crawford

Image: Nathan DeFiesta

So iconic was their hatred that it later inspired documentaries and TV series. Davis and Crawford didn’t just feud; they redefined what a Hollywood rivalry is. For decades, the two icons sparred over leading roles, critical acclaim, and public adoration.

Gossip included backhanded insults, stolen lovers, and outright sabotage during productions. When they finally shared the screen in 1962’s What Ever Happened to Baby Jane? , the film’s unsettling tension was magnified by their very real animosity.

12

Chevy Chase vs Bill Murray

Image: Aleks Dorohovich

In the early days of Saturday Night Live , Chevy Chase and Bill Murray were usually at each other’s throats. Chase’s sharp, polished delivery often clashed with Murray’s more offbeat, improvisational style, and the tension spilled offstage.

Reports of heated arguments (and even a near brawl backstage) turned their working relationship into one of the show’s most notorious conflicts. Though both later moved on, their rocky career start stands as a reminder of how fragile chemistry can be in comedy’s spotlight.

1

He was not allowed to attend school

Image: Hennie Stander

It was a different time back then, that is for sure. Because Hamilton’s parents were never married, he was barred from attending school . Fortunately, the young Alexander was privately educated and pored over his family’s collection of classics.

Despite being an orphan from an early age (his father abandoned the family when Hamilton was just a boy, and his mother died not long after), Hamilton stayed on course and remained an avid reader throughout his life.

2

His writing skills helped him leave the Caribbean

Image: Clark Young

Alexander Hamilton was born on the island of Nevis in the British West Indies. A letter he sent to his father detailing a hurricane that struck Saint Croix was reprinted in the Royal Danish American Gazette due to his remarkable penmanship.

The locals were so impressed by his style that they raised money to send Hamilton to a college in the British North American colonies.

3

Self-taught lawyer

Image: Tingey Injury Law Firm

Most people would have been happy with their lot in life if they were George Washington’s personal secretary, but not Alexander Hamilton. After resigning from his post, he was able to study law and passed a legal examination within six months in 1782 .

He had been reading law on his own in Nevis and at King’s College and had studied with John Jay and William Paterson, two future Supreme Court justices.

4

The bulk of the Federalist Papers

Image: Sear Greyson

Hamilton, along with Madison and Jay, was one of the three authors of The Federalist Papers , which helped secure the Constitution's ratification. Hamilton wrote roughly 51 of the 85 essays , which are still consulted today by scholars and the Supreme Court. However, Hamilton’s authorship of the documents wasn’t made public until after his death in 1804.

5

Founded the Treasury Department

Image: Alexander Schimmeck

When Washington became president, he appointed Hamilton as the first Secretary of the Treasury . Hamilton devised a solution to pay off the former colonies’ war debt and then organized the Treasury Department into a powerful unit.

Hamilton also formed the First Bank of the United States and helped convince other nations that the United States was financially stable.

6

Inspired the first American political party

Image: Adam Michael Szuscik

Hamilton’s work as Treasury Secretary and his advocacy for a strong central government led to the unofficial formation of the Federalist Party by 1791 . And, as often happens when a political party arises, a rival is quickly formed.

In response, leaders like James Madison and Thomas Jefferson created a political faction known as the Democratic-Republicans, which directly opposed Hamilton and his ideas.

7

Helped his political rival become President

Image: Alicia Razuri

In the 1800 presidential election, the House of Representatives, controlled by the Federalists, had two Republican candidates to choose from: Jefferson and Aaron Burr. In a private letter to a House member, Hamilton expressed his strong dislike for Burr .

"Mr. Burr loves nothing but himself—thinks of nothing but his own aggrandizement—and will be content with nothing short of permanent power in his own hands. In a choice of Evils, let them take the least—Jefferson is, in my view, less dangerous than Burr."

8

Received Washington’s last letter

Image: Valeria Reverdo

George Washington, the first president of the United States, sent his last written letter to Hamilton two days before his death on December 14, 1799. In it, Washington (who had been a mentor to Hamilton throughout his political career) praised his apprentice’s idea of establishing a national military academy.

Washington wrote to Hamilton that such an institution would be of "primary importance to the country."

9

Founded the New York Post

Image: Roman Kraft

Hamilton conceived his newspaper, originally called the New York Evening Post , as a megaphone for the anti-Jefferson Federalist Party , which he helped create. Hamilton himself wrote many of The Post’s early editorials.

The newspaper was founded in November 1801, and according to its editor, William Coleman, Hamilton personally wrote many of the editorials.

10

His son died in a duel, too

Image: GAIMARD

Just like his father, Philip Hamilton also received a mortal wound in a duel . This tragic event occurred three years before Alexander Hamilton’s own demise, under similar circumstances.

Both duels took place in Weehawken, New Jersey. In a cruel twist of fate, Alexander Hamilton even used the same set of pistols as his son.