5. "I'm Easy" from Nashville
Written and performed by Keith Carradine
Nashville is one of the masterpieces of the great American director Robert Altman. It follows 25 characters in the course of a day or two in, where else, Nashville, each one involved in country or gospel music. There are lots of original songs in this film, some of which were actually written by the actors themselves, including this one written by Keith Carradine which probably is the most popular of the bunch (and, IMO, at least, the best and probably the most memorable). It won the Oscar for Best Original Song.
4. "Beauty and the Beast" from Beauty and the Beast
Written by Alan Menken (music) & Howard Ashman (lyrics)
Performed by Angela Lansbury
Disney has given us a lot of great, memorable movie songs from "Zip-A-Dee-Doo-Dah" to "When You Wish Upon a Star" to "A Whole New World" and tons and tons of others but this one is probably my favorite. Such a simple, beautiful song that perfectly, perfectly captures the spirit of the great animated musical it was written for. It deservedly won the Best Original Song Oscar as well. I know there's a pop version performed by Celine Dion and Peabo Bryson but I think Angela Lansbury's version is the best.
3. "Mrs. Robinson" from The Graduate
Written by Paul Simon
Performed by Simon & Garfunkel
The Graduate is one of the most groundbreaking and definitive films of the 1960s and one of the things that helped it achieve its classic status is its fantastic soundtrack which deftly captured both the film and the era in which it was released. "Mrs. Robinson" is a classic movie song. However, it was not even nominated for an Oscar. Why? Because Paul Simon forgot to submit the proper paperwork. Oh, drugs.
2. "Moon River" from Breakfast at Tiffany's
Written by Henry Mancini (music) & Johnny Mercer (lyrics)
Performed by Audrey Hepburn
Breakfast at Tiffany's is director Blake Edwards' romantic-dramedy that's an adaptation of a work by Truman Capote. It stars Audrey Hepburn in one of her most famous roles. It's also where the song "Moon River" came from. It's a simple yet beautiful and moving song. It has been covered tons of times most famously by Frank Sinatra and Andy Williams. Audrey Hepburn sings it in the film and although she doesn't have the most perfect voice, she captures the song's moving simplicity and sweetness better than a lot of the singers that covered it subsequently.
1. "Over the Rainbow" from The Wizard of Oz
Written by Harold Arlen (music) & E.Y. Harburg (lyrics)
Performed by Judy Garland
You shouldn't be surprised. Personally, I don't think a Top 5 Movie Songs list has any credibility if this particular is not in there somewhere. It's probably one of the most beautiful songs ever written period. Yes, I'll say it and I'm not ashamed. Like "Moon River", tons and tons of singers have covered it but I think the best version is still Judy Garland's from the film itself. And to think, the studio heads almost cut this song out because they felt it slowed the movie down! That would've been tragic.