Midtown Happy Hour: Overlook Has a Great Early Happy Hour Slightly Out of Bounds

If you like to eat, chances are you like to drink (read: a lot of you are freakin’ lushes), so I thought maybe it was time to introduce a happy hour column to the site. Every week, our Happy Hour Correspondent posts about a different bar in Midtown that fits the Midtown Lunch mentality: unhealthy food, not lame (unless it’s lame in a cool way), and most importantly… cheap.

On my quest to find some decent places to grab a beer al fresco in honor of spring, I hit up Overlook (44th btw. 2nd + 3rd Ave.) a few times in the last few weeks to see what it has to offer. After my experience at Pod 39 Hotel/Salvation Taco’s rooftop lounge I was eager to find an outdoor spot that can pass the Midtown Happy Hour test of cheapness.

Overlook is a bar I had seen mentioned in Midtown Lunch but never covered. I wondered why, and it seems the place is slightly out of bounds. The good news is this: Overlook has one of the best deals for happy hour- two for one drinks! The bad news: it runs from 2:00 – 6:00. So it’s an early one, but it’s not often you can score a decent draft for $3. After 6:00, they offer weekday specials, but they aren’t that amazing.

The roof deck is hopping on a nice day, but it begs the question as to how Overlook got it’s name, and what exactly we’re looking over. There’s a few buildings and a vacant lot for a view on the 2nd floor roof deck, but don’t get too excited about the view. Lesson: don’t go to Pod 39’s rooftop lounge right before you go to the Overlook if you’re a skyline snob.

Downstairs is kind of fun too. Classic not classy — nothing pretentious. A great back room with walls decorated with originals from real cartoonists. From their website:

“Overlook’s first cartoon walls were drawn over a period of time during the late 1960′s by New York’s most prominent artists.

It is a reminder of the hayday of Costellos — a known haunt of New York City’s newspaper men.

Regarded by the national cartoon society as a historical treasure, the wall enjoys a prominent and affectionate display in Overlook.”

We were all happy with the food there too. The fries were addictive, with many different side dipping sauces to choose from like flavored mayos, dressings, and distinctive ketchups.

The wings would have been some of my favorites if the blue cheese wasn’t so lame (it tasted like it was straight from a generic grocery store bottle). At $8.99, they were cheap, decent sized, and there were ten of ‘em. The sauce (we ordered hot) had a great buttery flavor to it. And the wings were crisped to perfection. Carrots and celery accompanied the dish, which is always my preference.

So, to sum it all up, it’s a good place to go for outdoor drinking, decent food, and a good happy hour — if you can make it out of work that early.

The +

  • One of the best happy hour deals around with 2 for 1 drinks. Go Midtown Happy Hour!
  • Wings are my thing, and these are fabulous if you don’t care about the blue cheese!
  • I like that the fries have so many dipping sauces to choose from.
  • You can go outside and be in the air.

The -

  • The “Overlook” isn’t overlooking much.
  • Happy hour only goes from 2-6. That does me no good.
  • It’s slightly out of bounds.

Overlook, 225 E. 44th St., 212-682-7266

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