The tallest skyscrapers in the world, from 1895 on. All pictures link to a hi-res version (some link directly to the image; right-click > open in new tab to avoid slide show).

1895: Milwaukee City Hall, Milwaukee, USA (353 ft.)

1899: Park Row Building, NYC, USA (391 ft.)

1901: Philadelphia City Hall, Philadelphia, USA (511 ft.)

1908: Singer Building, NYC, USA (612 ft.) (to the left in the picture; Woolworth is in the background in 1913)

1909: Met Life Tower, NYC, USA (700 ft.)

1913: Woolworth Building, NYC, USA (792 ft.)

1930: Chrysler Building, NYC, USA (927 ft.)

1931: Empire State Building, NYC, USA (1,250 ft.)

1972: World Trade Center, NYC, USA (1,368 ft.)

1974: Sears Tower, Chicago, USA (1,450 ft.)

2004: Taipei 101, Taipei, Taiwan (1,474 ft.)

2008: Shanghai World Financial Center, Shanghai, China (1,599 ft.) (the one that looks like a bottle opener)

2010: Burj Khalifa, Dubai, UAE (2,717 ft.)

Related:

Pyramids vs. Skyscrapers

Vikram Mansharamani: Towering Indicators