This is the song he wrote for the movie "Postcards from the Edge" which got an Oscar nomination as Best Song, "I'm Checking Out" (of This Heartbreak Hotel"). It's really wonderful, and I think bowled people over how good Meryl Streep was singing it. And had no idea it was written by Shel Silverstein. It's a shame she didn't get to sing it live on the 1991 Oscar broadcast, since I think it would have blown the roof off the place. But she was late in her pregnancy, and wasn't allowed to fly. Instead, Rebecca McEntire sang it, and did a very good job. But...if only.
As I noted the other day, I have a sense that Shel Silverstein's involvement with the movie dates back to the 1950s in Chicago, since he's an unlikely choice to write the big closing song for the movie -- especially since the score was written by Carly Simon. Silverstein has long been a staple in the city, and Postcards from the Edge was directed by Mike Nichols who got his start also in Chicago as a member of the Compass Players, the precursor of The Second City, and as an announcer on WFMT classical radio. So, my guess is that he and Shel Silverstein became friends at the time and over the subsequent 40 years. And Nichols felt his old friend was the right choice to write the number.
The song didn't win. That went to "Sooner or Later" by Stephen Sondheim from Dick Tracy. It was perfectly good song, and deserving. But I much prefer "I'm Checking Out." My sense (right or wrong) is that "Sooner or Later" was helped by the fact it by by SONDHEIM and sung by MADONNA and had high cachet. Again, it's a good song. Mainstream (and I don't mean that pejoratively). Not more country. But this below is the song I would have preferred.
(It's the full song itself, but cuts off right before the joyous reprise and closing credits, which I'll embed, as well.)
By the way, for those who like to note such things, Shel Silverstein's credit for writing the song comes along at the 2:26 mark.
As a bonus, here's Reba McEntire's Oscar performance --
As as a quick additional bonus -- here's Meryl Streep at the premiere of her movie, One True Thing, when she spots Reba McEntire and goes over to thank her. (It comes around the 1:00 mark if you want to jump to it.)