Visible crew/equipment: In one shot when Annie and Walter are speaking in front of a shop window, you can see the cameraman's reflection. You even see him pivot his torso to follow the actors as they walk offscreen.

Sleepless in Seattle (1993)
Plot summary
Directed by: Nora Ephron
Starring: Tom Hanks, Bill Pullman, Meg Ryan, Victor Garber, Rita Wilson, Ross Malinger
Widower Sam Baldwin and his young son, Jonah, move to Seattle to start a new life. Lonely Sam is ready to start dating again, but still missing his mother, an upset Jonah calls a psychologist on a national radio talk show. Sam discovers Jonah is on the air. Sam gets on the phone and tells the psychologist that although it’s been tough, he and Jonah are doing OK. Single women across America hear Sam’s poignant story and write to him wanting to meet. East Coast reporter Annie Reed is also touched and believes Sam may be her soul mate. Even though she’s engaged to Walter, she sends Sam a letter. On the pretense of writing a story, she tracks down Sam’s address and goes to Seattle. Although she and Sam catch revealing glimpses of one another they do not meet, and Annie returns home.
Meanwhile, Jonah has read Annie’s letter, and he’s convinced she’s the one for Sam. Impersonating Sam, he writes Annie and suggests they meet atop the Empire State Building on Valentine’s Day. Sam finds out and has a talk with Jonah and thinks the matter is ended. Jonah is unfazed, however, and with the help of his playmate whose mother is a travel agent, books a flight to NYC to find Annie. A frantic Sam discovers Jonah is missing and follows him to New York.
Annie: This was mailed before I went to Seattle. Before the ho.





Answer: Ray Charles is the singer who performs this version of "Somewhere over the Rainbow" - this is not on the original movie soundtrack, but you may be able to find a Ray Charles album where this song is included.
I found an album by Ray Charles "Genius Loves Company By Ray Charles, Ray Charles And the Count Basie Orchestra" where "Over the Rainbow" is one of the songs, but it's not the same rendition as in the movie "Sleepless in Seattle." I can't fine the movie version anywhere.
Try the Ray Charles album "Genius Loves Company." It's a collections of duets and he sings "Over the Rainbow" with Johnny Mathis. It was supposedly recorded sometime between 2003 and 2004, but his lines sounds like what's in the film. So I don't know if it's just him reprising an older version he did that was used in the film, or if it's the older version with Mathis' lines mixed in. I couldn't find anything earlier.
Bishop73