Among the more than $260,000 raised by D.C. Council candidate Vincent Orange is $1,000 from one “Cleopatia Smiles” of New York, N.Y.

Who is “Cleopatia Smiles”?

This person shares an address with Gate Pass Entertainment, a “full service production company” led by Sidra Smith, whose “focus is managing special projects, development and the production of independent film and television programs; in addition to documentaries, special events and theater.”

Among the company’s film projects, according to its Web site: “Cleopatra, Smiles.”

Gate Pass’s connection to the District — and to Orange, running for an at-large seat in tomorrow’s special election — isn’t completely clear. Last March, the Cleveland City Council offered $1.2 million in loan guarantees to another New York production company for three films, including “Cleopatra Smiles.” But in October, the Cleveland Film News blog ran an item declaring the “Cleopatra Smiles” project “inactive ... due to a lack of available financing.”

Sean Metcalf, an Orange adviser, said that “Smiles” is both a person and a business — a movie project being handled by Smith, an “acquaintance” of Orange’s.

She joins some of the candidate’s law school buddies, who are also in the entertainment biz and supporting Orange, Metcalf said, “because they feel they are helping a great cause.”

“It’s a concerted effort by Vince to bring in his friends from L.A., New York and Atlanta for a production house,” he added. Metcalf declined to name names: “It gives away a little bit of our jobs plan. It boils down to bringing jobs back here,” he said. “There’s enough filming that goes on here that there should be a production company.”

It is not uncommon, of course, for related business entities to each give maximum donations. Local real-estate developers have made an art of it, actually, offering up maximum allowed donations via multiple holding companies established for particular projects. Orange’s campaign finance report, however, lists “Cleopatia Smiles” as an individual.

Voicemails and e-mail messages left with Gate Pass Entertainment last week and this afternoon have not been returned.

The mysterious Ms. Smiles is not the only irregularity on Orange’s campaign finance reports. One donor, Richard Evans of Camden Street SE, apparently gave Orange $2,000 — that’s twice the legal limit. Evans is also proprietor of New Columbia Solutions and NCS Systems, each of which also gave $1,000.

Metcalf said the Office of Campaign Finance had not informed the campaign of any problem with the donation, but he said that Orange would address any potential issue.

Orange was among the first to raise questions about D.C. Council Chairman Kwame R. Brown’s fundraising, which prompted an OCF probe into his 2008 campaign. That investigation revealed that hundreds of thousands of dollars in donations and expenditures went unreported.

A 2005 Washington Post investigation into spending by the D.C. Maternal and Child Health Administration highlighted Evans and his business, which billed the city $300,000:

Evans, a former massage therapist, opened an office-supply business out of his home in 2001. The business, New Columbia Solutions, has no warehouse or inventory, but it landed a series of blanket purchase agreements to provide Maternal and Child Health with promotional key chains, magnets and other handouts.

But in addition to those items, he billed the city for food, office supplies, computer equipment, furniture, televisions and other electronics, spending documents show.

But neither Evans nor the agency can produce records of how he was awarded the contract or any showing that the goods were delivered. Evans’s invoices lack the detail standard on government records and list only broad categories, such as $7,000 for “various paper supplies.” Evans said the supplies were delivered but he threw away the city’s orders and records showing that he had purchased the items. He said he also deleted e-mails and other computer records.

UPDATE, 8:55 P.M.: The post has been updated to clarify that Smith is the producer of “Cleopatra Smiles,” not Orange’s law school friends, who are also in the entertainment business, per Metcalf.