Continuity mistake: The bearded man sitting next to Jonah, on the flight to New York, is also seen sitting two seats away from Sam when he flies to New York chasing Jonah. The same guy is on two different planes at the same time.

Sleepless in Seattle (1993)
Ending / spoiler
Directed by: Nora Ephron
Starring: Tom Hanks, Bill Pullman, Meg Ryan, Victor Garber, Rita Wilson, Ross Malinger
Sam finds Jonah atop the Empire State Building. Just as they are about to leave, Annie arrives. She has broken off her engagement to Walter, and came in the hope Sam would be waiting for her. Annie and Sam know they are destined for each other.
Emily
Annie Reed: Now that was when people knew how to be in love. They knew it! Time, distance... nothing could separate them because they knew. It was right. It was real. It was.
Becky: A movie! That's your problem! You don't want to be in love. You want to be in love in a movie.
Join the mailing list
Separate from membership, this is to get updates about mistakes in recent releases. Addresses are not passed on to any third party, and are used solely for direct communication from this site. You can unsubscribe at any time.
Check out the mistake & trivia books, on Kindle and in paperback.
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