This is not an easy thing to do BUT we have, on many occasions, gotten what we needed. This is a long and detailed answer.
The physical address of Harpo Studios in Chicago is:
1058 W. Washington Blvd.
Chicago, Il 60607
Her new endeavor Oprah Winfrey Network (OWN) is rumored to be located in Burbank, CA. Because it takes over one of the Discovery channel's networks, it may be located in Silver Springs, MD.
It is never easy to get unsolicited materials to celebrities, of course, because there would be millions of pieces of mail, packages, et cetera.
We work frequently with and for celebrities and, if I were you, I would contact the studio and ask to speak with Ms. Winfrey's secretary. This, as is common in the media--- protecting their stars--- may be very difficult. Unless they know you or the media related company you work for, the call will not be put through.
One thing I have personally done is to gently and sincerely XXXXX XXXXX receptionist. Using phrases such as: " I really hope you can help me", "i've got a big challenge" et cetera, have opened countless doors to the people thet we or our clients needed to reach. If you don't really mean it, they'll now immediately.
Keep it brief and professional. Though your portrait is, I'm sure, very lovely, most production companies and celebrities refuse unsolicited deliveries immediately and return or REFUSE delivery of them at the door. Again for their protection.
Once you've buddied up with the receptionist (who will probably be insanely busy with hundreds of calls) see if they'll give you the name or department to which you may send a delivery. BETTER than that though, is to ask for the name of the person or departmenet to whom you could speak to seek permission to send the piece.
The rules are strict and there for the protection of the celebrity from untold thousands of persons who might not be as nice as you.
"You catch more flies with honey..." works for us very well.
Sometimes you have to be creative. For example: This is a link to a personal Oprah contact page on peekyou:
So to review:
1. Call the production company (NOT ON A MONDAY--- better a Wednesday or Thursday--- depending on when the show tapes).
2. Be just as sweet and professional and sane as you can be in order to win the trust and favor of the receptionist. You need to know who to ask for permission. They are probably the BEST person to provide that info. Let them know you need their assistance.
(BE PREPARED TO IDENTIFY YOURSELF, provide verifiable information, name, address, phone etc... they don't know who you are.
3. Be polite, professional and brief. Thousands of calls cross their lines from indutry professionals each day. If they seem a little annoyed, let them know you respect their time and don't mean to be a bother...but you need their help.
4. Once you have gotten permission to send the piece, which will then be expected (get the person's full name, department, extention or phone, confirm the address and indicate an approximate date of arrival so they'll be "looking" for it and won't refuse it.
5. Send it via an express delivery/overnight company and require a signature, OR send registered mail: receipt requested.
It's a lot to go through just to be nice and give a gift to someone. I'm sure you understand that unless you've got a connection, it's difficult (not impossible) to achieve celebrity access. These things have worked for me personally on many occasions. My job is to make our clients happy and to get them what they need/request. I really hope that they work for you.