1

Josephine Baker

Image: Richie Lugo

Josephine Baker was the first Black woman to star in a major motion picture , the 1927 French silent film Siren of the Tropics . During her early career, Baker was among the most celebrated performers to headline the revues of the Folies Bergère in Paris. Her performance in the 1927 revue Un vent de Folie caused a sensation in the city. Her costume, consisting only of a short skirt made of artificial bananas and a beaded necklace, became an iconic image and a symbol both of the Jazz Age and the Roaring Twenties.

Baker was celebrated by artists and intellectuals of the era, who variously dubbed her the "Black Venus," the "Black Pearl," the "Bronze Venus," and the "Creole Goddess." She aided the French Resistance during World War II, and after the war, she was awarded the Resistance Medal by the French Committee of National Liberation, the Croix de Guerre by the French military, and was named a Chevalier of the Legion of Honour by General Charles de Gaulle.

2

Rudy Vallée

Image: Matt Botsford

Rudy Vallée was the first male singer to rise from local radio broadcasts in New York City to national popularity as a "crooner." He had a thin, wavering tenor voice and seemed more at home singing sweet ballads than jazz songs. But his singing, saxophone playing, and the innovative arrangements he wrote for his band attracted the attention of a rapidly increasing number of listeners, especially young women.

Singers needed strong voices to fill theaters in the days before microphones. Crooners had soft voices that were suited to the intimacy of radio; the microphones, in this case, promoted direct access to "a vulnerable and sensuous interior," or, in other words, "a conjured intimacy." Vallée was one of the first celebrity radio vocalists.

3

Bobby Darin

Image: Jack Sharp

Bobby Darin was an American teen idol and, later, an adult crooner who, in 1958, co-wrote and recorded his first million-selling single, "Splish Splash," followed by "Dream Lover" and his covers of "Mack the Knife" and "Beyond the Sea," which brought him worldwide fame.

In the early 1970s, his health was beginning to fail due to a weak heart. The knowledge of Darin's vulnerability had always spurred him on to use his musical talent while still young. Darin died in 1973 at the age of 37 in a hospital recovery room after having open-heart surgery in Los Angeles.

4

Keely Smith

Image: Harry Shelton

American jazz and popular music singer Keely Smith performed and recorded extensively in the 1950s with her then-husband Louis Prima , and throughout the 1960s as a solo artist. The couple were stars in the entertainment business, including stage, television, motion pictures, hit records, and cabaret acts.

They won a Grammy in 1959, its inaugural year, for their smash hit, "That Old Black Magic," which remained on the charts for 18 weeks.

5

The Ink Spots

Image: Jorge Flores

The first band on the list, the Ink Spots was an American vocal pop group who gained international fame in the 1930s and 1940s due to their unique musical style, which predated rhythm and blues and doo-wop .

On January 12, 1939, the Ink Spots recorded "If I Didn't Care," one of their biggest hits, selling over 19 million copies and becoming the 8th-best-selling single of all time. Since they disbanded in 1954, there have been well over a hundred vocal groups calling themselves "The Ink Spots," with and without any original members of the group.

6

Ella Fitzgerald

Image: zachrie friesen

A frequent collaborator of the Ink Spots, Ella Fitzgerald was a singer, songwriter, and composer, sometimes referred to as the "First Lady of Song," the "Queen of Jazz," and "Lady Ella." She was noted for her purity of tone, impeccable diction, phrasing, timing, intonation, absolute pitch, and a "horn-like" improvisational ability, particularly in her scat singing.

Outside her solo career, she recorded music with Louis Armstrong, Duke Ellington, and the aforementioned Ink Spots. These partnerships produced songs such as "Dream a Little Dream of Me," "Cheek to Cheek," "Into Each Life Some Rain Must Fall," and "It Don't Mean a Thing (If It Ain't Got That Swing)."

7

Bing Crosby

Image: Alexander Wark Feeney

A one-man orchestra, Bing Crosby was a singer, actor, television producer, radio personality, and businessman. The first multimedia star , he was one of the most popular and influential musical artists of the 20th century worldwide.

In 1948, American polls declared him the "most admired man alive," ahead of Jackie Robinson and Pope Pius XII. That same year, Music Digest estimated that Crosby's recordings filled more than half of the 80,000 weekly hours allocated to recorded radio music in America.

Crosby is one of 33 people to have three stars on the Hollywood Walk of Fame , in the categories of motion pictures, radio, and audio recording.

8

Perry Como

Image: Oscar Sutton

Perry Como was an American singer, actor, and television personality who sold over 100 million records worldwide and pioneered a weekly musical variety television show. His weekly television shows and seasonal specials were broadcast around the world. He recorded primarily vocal pop and was renowned for his recordings in the intimate, easy-listening genre pioneered by our newly acquainted friend, Bing Crosby.

In the official RCA Records memorial in Billboard magazine, his life was summed up in these few words: "50 years of music and a life well lived. An example to all."

9

Nina Simone

Image: Artem Bryzgalov

A bigger-than-life figure, Nina Simone was a singer, songwriter, pianist, composer, arranger, and civil rights activist whose piano playing was strongly influenced by baroque and classical music, and accompanied by expressive, jazz-like singing in her contralto voice .

Early in her career, Simone played piano at a nightclub in Atlantic City, where she was told that she would have to sing to her accompaniment. This effectively launched her career as a jazz vocalist. Simone also became known for her work in the civil rights movement during the 1950s and 1960s, and she later fled the United States and settled in France following the assassination of her friend Martin Luther King Jr. in 1968.

10

Screamin’ Jay Hawkins

Image: Music HQ

The closer of this list is one of the most colorful characters in American music. "Screamin' Jay" Hawkins was a singer-songwriter, musician, actor, film producer, and boxer, best known for his powerful, shouting vocal delivery and wildly theatrical performances with macabre props onstage, making him an early pioneer of shock rock.

Screamin’ Jay’s most successful recording, "I Put a Spell on You," was created when the entire band was intoxicated during a recording session where "Hawkins screamed, grunted, and gurgled his way through the tune with utter drunken abandon." The resulting performance became his greatest commercial success and reportedly surpassed a million copies in sales.

1

The Big Apple: New York City

Image: Nik Shuliahin

Everybody knows "The Big Apple" refers to New York— the city that never sleeps . But why, exactly? Is it because there’s a worm (the subway) underneath it? Or is it a metaphor for something we strive for?

2

The Big Easy: New Orleans

Image: mana5280

It sure feels easy to stroll through New Orleans, a city known for its laid-back atmosphere and rich cultural energy, where jazz bands can spontaneously form on any corner and lively public celebrations are always just around the bend. But what’s the story behind its nickname?

3

Motor City: Detroit

Image: Doug Zuba

The most populous city in Michigan, the nickname "Motor City" certainly feels right for its bustling streets and large industrial background —but what exactly led to the adoption of this powerful nickname?

4

Sin City: Las Vegas

Image: Grant Cai

We all know the famous adage: "What happens in Vegas, stays in Vegas." Given the city’s notorious nightlife and gambling scene , it’s understandable—you might prefer to forget how you lost all your savings on a slot machine. But is that the only reason it earned its infamous nickname?

5

The Windy City: Chicago

Image: Ozzie Stern

Situated on the shores of Lake Michigan, Chicago's nickname might seem to stem from its exposure to harsh weather —but sometimes, the obvious answer isn’t the correct one. Is it really the weather, or is something stranger at play?

6

The Mile High City: Denver

Image: Emmanuel Appiah

Is Denver really a "Mile High" city because of its geographical proximity to the towering Rockies, or is it just a nod to its ever-expanding skyline? Keep reading to find out!

And now, the answers:

7

The Big Apple: Horse-racing origins

Image: Taylor Sondgeroth

The nickname originated in the 1920s as horse-racing slang , where "The Big Apple" informally referred to New York’s prize racetracks. Jazz musicians later popularized it, and a 1970s tourism campaign ultimately cemented it as a symbol of the city’s cultural and financial prominence.

8

The Big Easy: Chill and jazz

Image: Robson Hatsukami Morgan

If you followed our line of thought—you were right! This nickname emerged from the city's reputation for its relaxed lifestyle and vibrant jazz scene . While there are many theories about who first used the term—and whether it was originally meant to be derogatory—one thing is certain: all New Orleanians agree it 100% reflects the city’s unique blend of music, culture, and laissez-faire attitude.

9

Motor City: Infinite assembly lines

Image: Austrian National Library

Detroit earned its nickname as the birthplace of the American auto industry. Henry Ford’s revolutionary assembly line and the rise of car manufacturing giants cemented the city’s status as the global automotive capital of the 20th century. In fact, it remains home to the headquarters of America’s largest auto manufacturers—General Motors, Ford, and Chrysler.

10

Sin City: Prohibition defiance

Image: Jakub Dziubak

For a city founded by religious missionaries, "Sin City" is certainly an ironic nickname. In truth, its origins trace back to the construction of the nearby Hoover Dam in the 1930s. Thousands of workers flocked to the city in search of lodging and—presumably—entertainment. This led to the rapid rise of casinos and a thriving underground alcohol industry that—during Prohibition—was as profitable as it was illegal.

11

The Windy City: Long-winded speeches

Image: Kristina Paparo

While many assume it refers to Chicago’s weather, the nickname was actually coined by journalists mocking the boastful speeches of local politicians as they aggressively promoted the city as the ideal location for the World’s Fair. The term was meant to highlight the "hot air" of their rhetoric rather than the city's literal windiness.

12

The Mile High City: A matter of altitude

Image: Bill Griepenstroh

Denver sits exactly 5,280 feet — one mile — above sea level , earning its nickname, the "Mile High City," quite literally. Its natural elevation, combined with stunning Rocky Mountain views, makes it truly unique. Even more interesting, Denver’s altitude leads to some unusual effects: golf balls can travel up to 10% farther than at sea level, and alcohol tends to hit harder since high altitudes reduce the body's ability to process it efficiently.

1

Grand Canyon Railway

Image: Kurt Hänel

Can you imagine looking at the Grand Canyon National Park from aboard a train? You can do this, by taking the Grand Canyon Railway, which departs from Williams, Arizona, 30 miles west of Flagstaff.

This train travels past forests of ponderosa pines and parts of the Sonoran Desert into the heart of Canyon country, where you’ll spend the day exploring and hiking before boarding your return trip—just in time for sunset.

2

The Rocky Mountaineer

Image: Taylor Brandon

The spectacular views of Western Canada, along with the red rock wonders of Colorado and Southern Utah can be fully appreciated through the nearly all-glass cabins of the Rocky Mountaineer.

This luxurious train takes passengers from Denver to Moab, Utah, where they are treated to fine dining and cocktails while enjoying the majestic views.

3

Amtrak California Zephyr

Image: Levi Meir Clancy

Travelers aboard the California Zephyr can enjoy a 51-hour journey from Chicago to San Francisco that traverses through the magnificent landscapes of Colorado, Utah, Nevada, and northern California .

The ride passes through the Rocky Mountains, travels by the canyons of Colorado’s Western Slope, and spends an entire half-day on a trek through the Sierra Nevada, complete with views of Donner Lake and the Truckee River.

4

Cass Scenic Railroad

Image: Josh Nezon

The Cass Scenic Railroad was originally built in 1901 to transport lumber through the mountains of West Virginia . Today, it helps preserve the legacy of America’s locomotive history. The railroad offers two routes, including a four-and-a-half-hour round-trip journey to Bald Knob —the highest summit of Back Allegheny Mountain at 4,842 feet.

5

Amtrak Empire Builder

Image: Max Bender

The Empire Builder earns its name by traveling along major portions of the Lewis and Clark Trail. This 46-hour train departs daily from Chicago and traverses through Wisconsin, Minnesota, North Dakota, and Montana , before concluding in either Seattle or Portland .

Passengers on this less-crowded route can enjoy views of the Mississippi River and the North Dakota plains, as well as the stunning scenery of Glacier National Park in Montana.

6

Amtrak Southwest Chief

Image: Ezra Jeffrey-Comeau

The long road from Chicago to Los Angeles can be traveled in great style and comfort aboard the Southwest Chief. The train traverses more than 2,000 miles, passing through Illinois farmlands, the Mississippi River, the red mesas of New Mexico, and the Mojave Desert .

This 40-hour ride can be taken in its entirety or partially, but no serious view collector should miss the most scenic stretch, which spans Colorado, New Mexico, Arizona, and southern California, including Raton Pass—a National Historic Landmark along the Santa Fe Trail.

7

Cape Cod Central Railroad

Image: Melanie Hughes

This short, two-hour round trip is available only from May through October , immersing travelers in distinctive New England landscapes , including cranberry bogs, salt marshes, dunes, and woodlands.

The Cape Cod Excursion train offers an amazing sightseeing tour of the Cape’s natural attractions, including the charming Cape Cod Canal.

8

Amtrak Coast Starlight

Image: Lukas Robertson

This 35-hour journey between Los Angeles and Seattle departs daily and stops in some of the West Coast ’s greatest cities, including Santa Barbara, San Francisco, Sacramento, and Portland .

The southern half of the route features long stretches of the Pacific Ocean shoreline before moving inland to the valleys of the state’s agricultural heart, eventually reaching the snow-covered peaks of the Cascade Mountains. The observation lounge on the train offers the best views in the house.

9

Amtrak Adirondack

Image: Robert Macleod

The final Amtrak train on this list is the Adirondack. This route runs from New York City to Montreal, departing from the new Moynihan Train Hall at Penn Station. The 10-hour ride takes its passengers along the Hudson River up to Albany then passes through Saratoga Springs and Lake Champlain before arriving in Canada .

It is highly recommended to take this route in the fall during peak foliage season to watch New England’s changing autumn colors pass by your window.

10

Napa Valley Wine Train

Image: Daniel Salgado

Imagine being able to drink wine from the beautiful wineries in Napa Valley without worrying about who is going to drive. That is exactly what passengers of the Napa Valley Wine Train can do.

Originally built in 1865 by a local millionaire to transport visitors to a spa resort in Calistoga, the train now offers travelers the chance to sip local vintages from a luxurious railcar while passing vaunted vineyards on a three-hour round-trip journey .