1) Hong Kong, China

Hong Kong is number one on my list for many reasons: Hong Kong has a whopping 43 buildings over 200 metres tall, 30 of which were built in the year 2000 or later!!! It also boasts four of the 15 tallest buildings in the world… that's all in one city! Hong Kong’s skyline shows a large selection of distinct sky-reaching towers, with beautiful night lighting and reflection. This city exemplifies the post-modern skyscraper and skyline. Finally, the mountain backdrop makes this skyline the greatest on the planet!
Metro/Urban Population: 6.9 million

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2) Chicago, USA

Chicago is the birthplace of the modern skyscraper. When Chicago built its first steel high-rise in 1885, it was not the tallest structure in the world but the first example of a new form of engineering that would change nearly every city on earth. Chicago has 19 buildings over 200 metres tall (three of which are among the top 20 tallest buildings in the world, including the tallest in North America). Chicago has some of the finest mid-century architecture and examples of modern skyscrapers.
Metro/Urban Population: 8.7 million

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3) New York, USA

New York City has one of the densest and most diverse skylines, with a huge collection of buildings and building styles. Thanks to artist's and Hollywood’s obsession with the city, it is also the most easily recognizable skyline in the world. New York City has an amazing collection of 47 buildings that stand over 200 metres - the most in the world! The four tallest buildings in NYC were all built in the early 1930s! Home of the famous, now destroyed World Trade Center Towers, the Empire State building, the Statue of Liberty and the United Nations, New York City is the financial capital of the western world. New York's skyline is probably the most compact and overwhelming collection of architecture from almost any point in the city.
Metro/Urban Population: 21.0 million

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4) Shanghai, China

Not to be mistaken for a space station, Shanghai is a real city! China's biggest and most advanced city, Shanghai was said to be the most modern cities at the turn of the 20th century, but lost its glory. It is now quickly regaining its position as one of the biggest economic powerhouses in the world as well as a showcase of modern architecture and a sky reaching array of buildings, that deck the edges of the semi-circular shoreline. In Shanghai you’ll find 28 structures that are over 200 metres tall and two over 400 metres including one that is insanely tall (468m), the Oriental Pearl TV Tower.
Metro/Urban Population: 13.1 million

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5) Singapore, Singapore

One of the best (urban) planned and cleanliest metropolitan cities in the world, Singapore looks like an architectural model city come to life. The buildings cannot be higher than 280 metres due to air traffic control restrictions, but that has added a tall (but not too tall) and consistent building height and space pattern that makes this skyline unique: Three buildings are exactly 280 metres tall and 5 others (8 total) stand at just over 200 metres. The buildings are mostly light-coloured and there is a large expanse of greenery dotted around the city core. This South-Eastern city is definitely in a league of its own.
Metro/Urban Population: 3.8 million

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6) Tokyo, Japan

Tokyo is the world's most populated city. Its skyline has a number of unique characteristics that set it apart from other big city skylines, among them 15 structures at over 200 metres tall (including the Tokyo Tower which changes colors every night). But because of the density and vast size of the city, every corner appears to have its own skyline. With the height restrictions and the required red lights that flash atop all mid to tall-sized buildings make the city look spectacular at night. Tokyo is filled with neon lighting and unique, contemporary architecture, and like New York City is also often portrayed in movies for its aesthetic and eye-catching cityscapes. Interesting fact: Tokyo houses the world's largest fleet of helicopters to get around town if traffic gets too crazy.
Metro/Urban Population: 32.0 million

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7) Toronto, Canada

Toronto is a meeting place, a crossroads of many cultures and ethnicities. Toronto is downtown Canada, the biggest city in the country with a skyline to match. Toronto has 7 structures in its skyline that stand at over 200 metres, including the astonishingly tall 553 metre, CN Tower, which is often referred to as the tallest free-standing structure in the world. The CN Tower possess the world's highest observation deck, making this city's skyline one of the most immediately identifiable.
Metro/Urban Population: 5.5 million

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8) Kuala Lumpur, Malaysia

This is probably the most impressive city worldwide that has less than 2 million residents. Marvelous modern buildings reach the sky here, and while the skyline is not too dense, it does allow buildings to soar and stand out. Kuala Lumpur has three of the 25 tallest buildings worldwide, including the tallest twin buildings, the Petronas Towers (which are considered by some to be the second and third tallest overall in the world), as well as the peaking, 420 metre Menara Kuala Lumpur Tower.
Metro/Urban Population: 1.6 million

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9) Seattle, USA

Seattle is the commercial, cultural and advanced technology hub of the Northwest USA and a major port city for Pacific and European trade. Home 4 buildings over 200m and the famous 184m Space Needle observation tower, Seattle is surrounded by mountains and water and offers some picture-perfect views. Seattle is commonly referred to as the Emerald City and renowned as a great social and corporate city with great planning. 
Metro/Urban Population: 3.7 million

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10) Shenzhen, China

What was a tiny fishing village on the border of Hong Kong in 1970 is now a buzzing metropolis of over six million people! Already containing 18 buildings at over 200 meters tall, including the Shun Hing Square (the 8th tallest building in the world), Shenzen is a spectacle of lights and neo signs after sunset, you can’t help but ask yourself... if you are in a video game or in a real city.
Metro/Urban Population: 7.2 million

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11) Dubai, United Arab Emirates

Is this a mirage in the Middle East? Seemingly out of nowhere emerges a city in the middle of a desert. This is Dubai, a city that produces only the best modern architecture in the world. Already home of the world's tallest all-hotel building and the tallest all-residential building in the world, AND currently proposed to build the world's tallest building, this skyline might just leap to the number 1 spot in the near future. While the skyline is not so dense, each building is a marvel all on its own. As a skyline it probably can't compete with the larger cities, however the individual buildings in this city are by far the greatest examples of modern architectural accomplishments. All seven structures in this city at over 200 metres tall were built in 1999 or later - that's how new this city is.
Metro/Urban Population: 1.5 million

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12) Seoul, South Korea

This city's skyscrapers are divided into many clusters, spread amongst the main businesses and residential districts. Most of the recent growth in Seoul's skyline, however, has been of residential towers over 60 storeys high that are shooting up like blades of grass! There are 10 buildings in Seoul over 200 meters tall and much of the mid-rise to high-rise structures are lined up in a linear fashion, creating a "wall" of buildings like no other. Seoul is where the ancient Eastern world meets the modern West.
Metro/Urban Population: 20.8 million

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13) Frankfurt, Germany

Certainly one of Europe's most interesting cities in terms of skylines, Frankfurt is home to five structures that are over 200 metres tall. These modern skyscrapers are marvels compared to those other, mostly non-existent ones scattered across European cities. The contrast here is interesting: The city combines low-rise, high-density traditional European architecture (some of which is over 1,000 years old), with modern towers that stick out like sore thumbs, but are impressive nonetheless.
Metro/Urban Population: 4.1 million (region)

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14) Sydney, Australia

Australia’s showcase city, Sydney has one of the most recognizable skylines due to its world-famous harbour, often referred to as the most beautiful natural harbour in the world. The Sydney Harbour has many bays and inlets. It is spanned by the monumental Harbour Bridge, and the Opera House sites on the shoreline like a white flower. The Sydney skyline is world-class with hundreds of skyscrapers in the central business district and many more high-rise buildings in the outlying neighbourhoods. Sydney has 8 buildings over 200 metres tall.
Metro/Urban Population: 4.2 million

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15) Dallas, USA

The "Big D", is a major inland American city. The city and metropolitan area lies amidst vast, high, and varying rolling prairies - with hundreds of large & small lakes, rivers, creeks, waterways and meanders. But Dallas; downtown is the center of the Forth-Worth-Dallas Metro Region which is home to 5.9 million people. Dallas' skyline is home to 7 buildings over 200 meters and the 187m Reunion Tower which looks like huge sphere of light! The skyline is very distinctive at night as it building lighting is very colorful, particularly with lots of green.
Metro/Urban Population: 5.4 million

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HONORABLE MENTIONS

16) Sao Paolo, Brazil

“What building did you say they lived in?” Finding it in the largest mass of condensed apartment buildings anywhere would be like finding a needle in a haystack. Sao Paolo has a population of over 18 million people! While the buildings are not super tall (with only a single structure at over 200 meters tall) this skyline is nevertheless completely and utterly stacked. Sao Paolo has a fleet of over 500 helicopters, the second largest helicopter fleet in the world, because if you want to get around by roads, they are as packed as the dense skyline.
Metro/Urban Population: 18.3 million

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17) Guangzhou, China

Guangzhou is a very modern city, yet it is called "the City of Flowers,” as each of its spectacular skyscrapers is surrounded by grand green spaces and flower beds. Although it only has six structures at over 200 metres tall, there are plenty of other high-rises, each displaying a design that stands out in its own respect. This includes the 391 metre, 80-floor, CITIC Plaza which appears transparent against the (usually) clear blue sky!
Metro/Urban Population: 4.1 million

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18) San Francisco, USA

Although SF has a large population in outlying regions, "The City", itself is densely packed into a compact area of a peninsula. This makes it the second densest city in the USA, next to NYC. Another North American skyline with little recent development, but still home to the classic Transamerica Pyramid (an architectural classic) is one of the three 200 towers over 200 metre. The famous golden gate bridge and surrounding water and mountains makes this skyline dazzling from almost any angled it is looked at from.
Metro/Urban Population: 7.7 million

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19) Pittsburgh, USA

Although Pittsburgh only has two buildings over 200m tall, its skyline is very impressive nonetheless. Pittsburgh has nicknames like the "city of bridges", "the Burgh" or the "golden triangle" which outlines its true characteristics. It is surround by three rivers and the CBD is shaped in a triangle and surrounded by golden color bridges. The city is also surrounded by hills and valley's giving access to great views of the city. The city has not had a major skyscraper raised since 1988, but good planning and a scenic surrounding region still makes it a great skyline.
Metro/Urban Population: 2.4 million

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20) Houston, USA

Everything is bigger in Oil-town Texas!! With 14 post-modern and individualistic skyscrapers over 200 meters, Houston is only beaten by the top 5 cities on this list in that category. Houston is built on a major port, but what is interesting is its lack of zoning restrictions, which has allowed major skyscrapers to be built all over the city in a scattered fashion. In fact, the tallest building in the United States outside a financial district in a major downtown is the Williams tower.
Metro/Urban Population: 5.2 million

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