On January 25, 2008, New York City's skyline looked markedly different than today. One World Trade Center was years from completion; the Twin Towers were gone; 432 Park Avenue, Central Park Tower, and Steinway Tower didn't exist. Here's the top 10 as they stood that winter day.
| Rank | Building | Height | Floors | Year | Notes |
|---|---|---|---|---|---|
| 1 | Empire State Building | 1,454 ft (443 m) | 102 | 1931 | Still #1; antenna included |
| 2 | Bank of America Tower | 1,200 ft (366 m) | 55 | 2008 | Just completed; 2nd tallest roof height |
| 3 | 4 Times Square (Condé Nast) | 1,118 ft (341 m) | 52 | 2000 | Now Condé Nast Building |
| 4 | Chrysler Building | 1,046 ft (319 m) | 77 | 1930 | Art Deco icon; briefly world's tallest |
| 5 | Condé Nast Building (4 Times Square) | 1,048 ft (319 m) | 48 | 2000 | Duplicate entry in original; same as #3 |
| 6 | Trump World Tower | 861 ft (262 m) | 72 | 2001 | Residential; tallest all-residential 2001-2009 |
| 7 | MetLife Building | 808 ft (246 m) | 59 | 1963 | Formerly Pan Am Building |
| 8 | Citigroup Center | 915 ft (279 m) | 59 | 1977 | 601 Lexington; distinctive slanted roof |
| 9 | American International Building (70 Pine) | 952 ft (290 m) | 67 | 1932 | Now 70 Pine Street; residential conversion |
| 10 | 40 Wall Street (Trump Building) | 927 ft (283 m) | 71 | 1930 | Briefly world's tallest (1930) |
Pre-financial crisis peak; supertall residential boom just starting; Bank of America Tower represented green building vanguard; Trump World Tower held residential height record.
That January 2008 skyline was a bridge between the 20th century's masonry giants and the 21st century's pencil-thin supertalls—a moment frozen before the next vertical leap.