1. PENN STATION COMPLEX, Midtown, including Madison Square Garden and 2 Penn Plaza, by Charles Luckman Associates (1968): We tore down McKim, Mead and White’s Pennsylvania Station for this?
2. PARAMOUNT PLAZA, at 1633 Broadway, by Emery Roth & Sons (1968): A cheap black box with glitzy stainless-steel suspenders set behind a windswept plaza with two inexplicable holes in the ground.
3. ONE ASTOR PLAZA, at 1515 Broadway, by Kahn & Jacobs, with chief designer Der Scutt (1969): Infamous for its crown of rabbit ears, and just as clumsy on the ground, where the hulk dominates Broadway.
4. 1185 SIXTH AVENUE, by Emery Roth & Sons (1971): The most offensive of the long line of offenders along Sixth Avenue north of 42nd Street. Mean, ugly, and big.
5. NEW YORK TELEPHONE COMPANY BUILDING, 1095 Sixth Avenue, opposite Bryant Park, by Kahn & Jacobs (1974): This bland tower makes an unsuccessful try at collaging three architectural scales together—medium, tall, and Goliathan—to warm up the company’s image. Cold to the touch; needs a face-lift.
6. THE EX-AT&T BUILDING (1984), 33 MAIDEN LANE (1986), and 885 Third Avenue, a.k.a. the LIPSTICK BUILDING (1986): The worst of many by architecture’s Public Enemy No. 1, Philip Johnson, the cynic who believes in no style but practices them all.
7. 60 WALL STREET, by Kevin Roche (1989): A gargantua set within downtown’s fragile street network, its façade detailed whimsically to look like a column. Ha ha.
8. ONE WORLDWIDE PLAZA, at 935 Eighth Avenue, by Skidmore, Owings & Merrill (1989): Guilty of postmodernist me-tooism—a middlebrow attempt at ye olde Ralph Lauren. Complete with a failed English-style shopping gallery at its base. Wrong city, wrong century.