Skyscrapers with free views?
 

Ideally something I can walk in and take the elevator to the top floor with no questions asked.

Not in this day and age.

Doesn't the Marriott in Times Square have a top floor bar? I believe 230 5th does as well.

Not the tallest buildings in the city, but definitely a different view.

Excellent suggestion. If the OP googles "NYC rooftop bars," I suspect s/he'll come up with other options, as well.

The Marriott bar is a decent view in most directions. My recollection is that the southerly view is blocked by another building, so you won't see much of lower Manhattan. Plus, given the cost of drinks and/or apps there, I wouldn't call it "free"! Other rooftop bars may be closed for the season (46 Mad, for example).

The AVA Lounge at DREAM Hotel (55th & Broadway) has a nice Times Square view.

The Lobby Lounge and MOBar in the Mandarin Oriental both have pretty decent views. The views aren't like Top of the Rock or the ESB and drinks aren't cheap, but both are beautiful spaces and you could probably wander around a bit and check out the view and leave without having to buy anything.

If you really want a view, though, the Top of the Rock is the way to go. It's worth the admission ticket.

Many of the hotels are good choices, you may not be able to get up to the roof, but usually at the upper floors there's a window or two by the elevator to let some light in.

Many are guest only and they check downstairs, but some are not.

No clue about most of these places, but they were listed in a NY Times story a few years ago and may be worth checking out to see if they are in a 4 or a 40 story building

Twenty-EightRooftops

A60 at the 60 Thompson Hotel, 60 Thompson Street between Spring and Broome Streets; 212-431-0400; www.thompsonhotels.com. Hotel guests and members only.

Ava Lounge, 210 West 55th Street; 212-956-7020; www.avaloungenyc.com.

BED New York, 530 West 27th Street; 212-594-4109; www.bedny.com. Serves dinner and Sunday brunch.

Boogaloo, 168 Marcy Street between Broadway and South Fifth Street, Brooklyn; 718-599-8900. Rooftop is accessible through a rocket-ship-like tube and open Thursday through Saturday.

Bookmarks, the Rooftop Lounge at the Library Hotel, 299 Madison Avenue at 41st Street; 212-204-5498.

Broadway Bar and Terrace, 226 West 52nd Street; 646-459-5820.

Buster's Garage, 180 West Broadway between Leonard and Worth Streets; 212-226-6811; www.bustersgarage.com.

Cabanas at the Maritime Hotel, 88 Ninth Avenue between 16th and 17th Streets; 212-835-5537; www.themaritimehotel.com.

The Delancey, 168 Delancey Street between Attorney and Clinton Streets; 212-254-9920; www.thedelancey.com. View of the Williamsburg Bridge.

The Eagle, 554 West 28th Street between 10th and 11th Avenue; 646-473-1866; www.eaglenyc.com. Gay leather and Levi's scene; barbecue Sundays from 5 p.m.

Heights Bar and Grill, 2867 Broadway between 111th and 112th Streets; 212-866-7035; www.heightsnyc.com. Near Columbia University.

Jade Terrace at the China Club, 268 West 47th Street; 212-398-3800; www.chinaclubnyc.com.

Latitude, 783 Eighth Avenue between 47th and 48th Streets; 212-245-3034; www.latitudebarnyc.com.

Local West, 1 Penn Plaza at Eighth Avenue and 33rd Street; 212-629-7070; www.localcafenyc.com. Across the street from Madison Square Garden.

Me Bar at La Quinta Inn, 17 West 32nd Street between Fifth and Sixth Avenues; 212-290-2460. Great Empire State Building view.

Metro Grill Roof Garden at the Hotel Metro, 45 West 35th between Fifth and Sixth Avenues; 212-279-3535; www.hotelmetronyc.com. Closed weekends.

The Roof Garden at the Metropolitan Museum of Art, 1000 Fifth Avenue at 82nd Street; 212-879-5500; www.metmuseum.org.

The Park, 118 Tenth Avenue between 17th and 18th Ave; 212-352-3313, www.theparknyc.com. Rooftop penthouse with hot tub complements the 4,000-square-foot ground-floor garden.

Pen-Top Bar at the Peninsula Hotel, 700 Fifth Avenue at 55th Street; 212-956-2888; www.newyork.peninsula.com.

Plunge at the Gansevoort Hotel, 18 Ninth Avenue at West 13th Street; 212-206-6700; www.hotelgansevoort.com.

Rare View at the Shelburne Murray Hill Hotel, 303 Lexington Avenue at 37th Street; 212-481-1999; www.affinia.com.

Red Sky, 47 East 29th Street between Park and Madison Avenues; 212-447-1820; www.redskynyc.com. Third-floor roof deck.

Sky Terrace at the Hudson Hotel, 356 West 58th Street; 212-554-6000; www.hudsonhotel.com. For hotel guests only.

Sushi Samba 7, 87 Seventh Avenue South at Barrow Street; 212-691-7885; www.sushisamba.com.

The Terrace at Sutton Place Bar and Restaurant, 1015 Second Avenue between 53rd and 54th Streets; 212-207-3777; www.suttonplacenyc.com.

13, 35 East 13th Street at University Place; 212-979-6677; www.bar13.com.

Top of the Tower at the Beekman Tower Hotel, 3 Mitchell Place at 49th Street and First Avenue; 212-980-4796; www.affinia.com. Old-school top-floor bar has two small outdoor areas.

230 Fifth, 230 Fifth Avenue at 27th Street; 212-725-4300.

Small building (not a sky scraper) but fun bar. They used to have Ally McBeal nights—definitely a fun place to watch that short-lived show. :D

These 4 I pulled out as not being much more than a floor or two up. Probably not worth it to visit.

Plunge @ Gansevoort is a better bet in the Park/Maritime 'hood, though the drinks are rather over-priced, even by NYC standards, and it can get quite crowded.

Thirty years ago, in my Jr High and HS days, we used to play the free view game. We'd pick a random skyscraper and ride the elevator to a random floor near the top. Whatever company was there became our "research topic". For example, if the elevator doors opened to Banco Nacionale de Brazil, then we'd tell the receptionist we were doing a term paper on Latin American Finance Systems, and do you have any materials you can give us? Usually, the receptionist would be befuddled by the unusual in-person request, and head to the back for a few minutes to find some assistance, some brochures, whatever, and we would just wait in reception and enjoy the typically spectacular views of the city. :D

Sadly, I'd imagine 21st century security rules and lobby checkpoints prevent todays youth from enjoying similar misadventures.