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.
Continuity mistake: When Jonah and Sam are seeing Victoria off at the airport, where does she go? During the scene other people are moving towards and around the door that Victoria seems pointed towards; however, in the shot that immediately follows her departure the doors are opened by the flight crew and passengers (including Annie) disembark. (01:04:15 - 01:05:25)
Continuity mistake: In the dinner scene, when Sam is discussing the topic of movies with Suzy, notice the drink glasses. The amount of wine in the glasses change several times throughout the scene.
Continuity mistake: Annie is discussing her trip to Seattle with Becky at her house. She pulls out the tape of "An Affair to Remember", walks into her kitchen, and Becky puts Annie's things on the table, handbag on the left and the purse to the right. They go back to the living room, then return to the kitchen a couple of minutes later. In the shot when Annie puts her mug down, the purse is now on the left and the handbag is on the right. (01:12:40 - 01:14:30)
Continuity mistake: Near the end, Annie and Walter go to a restaurant with a view of the Empire State Building. It is very cloudy, dark and grey in this shot. Just prior to this, Jonah is atop the Empire State Building and it is relatively clear. Later when Sam comes into New York it's cloudless again.
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