Ooh! Fun question!
Dead:
1) While everyone else has been saying "Helen Keller" the person I most want to meet is Annie Sullivan. Without HER there wouldn't have been a Helen Keller.
2) Eleanor Roosevelt
3) Katherine Hepburn (my mother "sort" of met her once when she and her sister went shopping for a mattress at the store Mom was a decorator for)
4) My maternal grandmother. She died before I was born and when I reached my twenties a lot of my actions and speaking habits had my mother swearing that I was her Mom reincarnated.
5) Mark Twain. Because, darn, he was funny if depressed as all get out.
6) William Butler Yeats. I never liked his poetry, but he was pretty and I'd like to know if the story about him and Georgie is true.
7) Mother Teresa...because...

Bernadette Soubirou (sp?) I can't tell you how many times I have seen The Song of Bernadette.
9) Florence Nightengale, Clara Barton and Linda Richards. I so admired them as a girl that I went into nursing school without even thinking that I may not have the courage and fortitude they had. I've always regretted that I couldn't follow in their footsteps. On the other hand, I am not sure they'd want to be librarians.
10) Harry Chapin, so I could tell him how much I enjoyed his music.
11) Sojourner Truth-"Ain't I a Woman" gets me every time I hear it read or read it myself.
12) Rose Wilder Lane-To learn if the rumors are true that she may have ghost written a number of her Mom's books.
13) Lucy Maud Montgomery-Ann of Green Gables--what more is there to say?
14) Louisa May Alcott-More than anyone, she inspired my love of the written word. I want to thank her.
15) Silly things: I'd just like to know whatever happened to Judge Crater and Jimmy Hoffa.
ETA: I have no idea why Bernadette has an emoticon with the sunglasses next to her...I put in a number 8, I swear!
LIVING
1) Tanith Lee--I loved her early books and still do. But the current ones...!!!!
2) Jean Stapleton--terrific, funny actress.
3) James Earl Jones. Actually, all I really want is for James Earl Jones to read the telephone directory to me. Or the Bible. Or any other large, thick tome that would require his wonderful voice to flow 'round me for hours.
4) Emma Thompson. LUnch with Emma Thompson would have to be a riotous funny affair, no?
5) Michael Feldman of "What Do You Know"--I love that radio show. It makes me laugh when I need to.
No one else comes to mind at the minute. I'm not as into current political scene as I am into past historical scene