They look like fortresses. And in many ways, they are. The Velvet Cloak inn on Hillsborough Street in Raleigh, and the old Jack Tar motel, aka the “Oprah Building” in downtown Durham, are two of the most mysterious, yet iconic structures in their respective cities. And the stories behind them are equally intriguing, mysterious and complicated.

Both enjoyed heydays. Celebrities and politicians kicked back and held court at the swanky, elegant Velvet Cloak Inn.

In the 1960s, the Jack Tar motel was considered swinging and modern, with promises to pamper its visitors with amenities such as a rooftop swimming pool.

Both buildings have deteriorated. But both have promise.

In the case of the Velvet Cloak, the Smoot family, which owns the property, has been sued by several residentsmany of them elderly or disabledwho allege they’ve been swindled. Two state agencies are investigating the Smoots for possible improprieties.

But for Raleigh, the Velvet Cloak troubles has larger implications. The building is located on a prime piece of land on Hillsborough Street, an area that is rapidly developing. That is, except for Velvet Cloak, which is stuck in time and a legal morass.

As for the Jack Tar, its decline began in 1977 when the motel closed. In 1995, Ronnie Sturdivant bought the old motel, and over the past 20 years, the building has succumbed to neglect. This happened even as the Sturdivant familyRonnie died in 2008, leaving the property to his heirshave charged veterans, the disabled and the down-and-out as much as $500 a month to live illegally in a run-down flophouse: a flophouse that has operated just two-tenths of a mile from City Hall and in the midst of an economic and cultural upswing in downtown Durham.

Now Austin Lawrence Partners, the developer behind the City Center Project a 26-story skyscraper, plus the reconstruction of several crumbling structures on Parrish and Main streetsplans to restore the Jack Tar to its former glory.

Even in their forlorn state, the Velvet Cloak and the Jack Tar nonetheless contribute to their communities’ sense of place. How these buildings are renewed will change that sensibility, hopefully for the better.

Still, many of us will miss passing by the Velvet Cloak Inn, remarking on its creep factor and speculating on what must go on behind closed doors.

And in Durham, the Jack Tar is an architectural anomaly that critics often dismiss as ugly. But the old motel will grow on you. Just give it time.