Your Top 5

Academy Award Winning Songs

Your Top 5 was born out of my love of music and reading and the book and film High Fidelity. Each week, I ask a new guest to give me their top 5 tracks, albums or artists relative to a topic.

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Dylan’s Oscar has been a constant on the Neverending Tour since he won it in 2000.

I am a bit of an amateur cinephile—more into the pop culture, writing, and musical elements present in films rather than some of the other attributes that film nerds go crazy over. It is nice to learn and know a little more about what I have watched or am watching. This past summer I read Quentin Tarantino’s book, Cinema Speculation, knowing full well that I was out of my depth, but did I learn a lot of fun “New Hollywood” facts about several movies I enjoy as well as watched some I had never heard of or seen.

I have been reading Dan Pal’s excellent Substack, PalCinema, Television, & Music , and decided that I would ask him to join me on one of these top 5 adventures. I even wanted to throw one right into his wheelhouse and discuss our top 5 Oscar winning songs. Selfishly, I wanted a chance to talk about Bob Dylan in my section as well. Let’s see what Dan has for us first, shall we?

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Dan’s Top 5

I was thrilled when Chris asked me to do a film related Top Five. Being that it’s the end of the year and several songs are being considered for this year’s Best Original Song Oscar, I thought going back through time to find my five favorite Oscar-winning songs would be an easy task. As I went through the list I only found one though that ended up on my Top Ten songs lists that I’ve been documenting on my PalCinema, Television, and Music Substack site this year. There are about 28 others that I find decent but narrowing down to the Top Five was tough! I rarely listen to any of these songs and find most have been overplayed. Maybe it’s because they were so associated with their films and often major hits, I feel less personally connected to most of them. However, being the list maker that I am, I plunged ahead with the task at hand. Most of my choices come from the 70s, a decade which offered some great movie songs that were worthy winners. The 80s were pretty good too and the majority of them were also major Top 40 hits. The 90s’ winners were a bit too Disney for my taste and the 2000s included songs that are pretty unmemorable. Nevertheless, here are my Top Five:

Number Five: Last Dance (1978) – Donna Summer, from Thank God It’s Friday

In a year when “Hopelessly Devoted to You” and “Ready to Take a Chance Again” would have also been worthy winners, “Last Dance” seems like a revelation for the Academy. After most years featuring ballads as winners (The Theme from ‘Shaft’ being a notable exception), a disco song capturing the top prize was pretty special. This was the song that allowed Donna Summer to hit with a song in which her vocals were strong and confident as opposed to the breathy work she did on her other big hits up until this point, “Love to Love You Baby” and “I Feel Love.” “Last Dance” deservedly won her a first Grammy. It’s been played at bars and weddings ever since.

Number Four: The Way We Were (1973) – Barbra Streisand, from The Way We Were

It features one of the most beautiful melodies and vocal performances ever and became Barbra Streisand’s first number one hit. This song was everywhere in 1973 and ’74. My mom was a huge Streisand fan and played her music throughout our house, especially this one. I think everyone can relate to the idea of looking back at memories with a mix of joy and sadness. (Heck, I’ve spent most of this year writing my own memoir!) Every line rings true. I especially like: “Can it be that it was all so simple then? Or has time rewritten every line? If we had the chance to do it all again tell me, would we, would we, could we, could we? Memories…may be beautiful and yet what's too painful to remember we simply choose to forget…” It doesn’t get any better.

Number Three: Evergreen (1976) – Barbra Streisand, from A Star is Born

I debated putting two Streisand songs in my Top Five but these two truly are great, plus she co-wrote and won an Oscar for this one. It was another big number one hit the year it won and if you think about the climate of Top 40 radio at the time it made sense. What we now call “classic rock” clashed with disco and a lot of adult contemporary songs. The film and its accompanying album were huge. This one also has a beautiful melody but rather than focus on the past it remains in the present as a very romantic and promising love ballad. Of course, Streisand’s vocal was again at its peak making for a truly emotional and heartfelt Grammy winning performance.

Number Two: Over the Rainbow (1939) – Judy Garland, from The Wizard of Oz

Before there was Wicked there was The Wizard of Oz, which played once a year on television when I was growing up. We always knew what Garland as Dorothy was singing about, with Toto nearby, as she so passionately sang about a world far, far, away. It’s another song of hope for a better place where “skies are blue” and “the dreams that you dared to dream really do come true.” After seeing the film once, we also knew what was coming within the beauty and drama of Munchkinland and Oz. So, listening to Garland sing provided high anticipation for that next chapter. The fact that the song also became a symbol for the LGBTQ community makes its relevance even more important to consider. It’s one of the great songs of all time.

Number One: Raindrops Keep Fallin’ On My Head (1969) – B.J. Thomas, from Butch Cassidy & the Sunshine Kid

This might not be everyone’s choice as one of the great winners of all time or even one that relates well to the film in which it was featured, but I’ve always loved it. I have great memories of listening to it as a child as we would drive up to a family farm in Northern Wisconsin. Hearing it always made me smile. It’s another song that is optimistic and hopeful in spite of the rain falling on our heads: “Raindrops keep falling on my head, but that doesn't mean my eyes will soon be turning red, crying's not for me, 'cause I'm never gonna stop the rain by complaining, because I'm free, nothing's worrying me.” My father had died the year this song and movie were released and I guess on some level I also think about it in relation to my mom who, while in the process of grieving, still picked herself up and moved forward with her life in spite of the tragedy.

Some other nominated songs that didn’t win but would have been made worthy winners include: “That’s Amore” (1953) from The Caddy, “The Man That Got Away” (1954) from A Star is Born, “What’s New Pussycat” (1965) from What’s New Pussycat, “Georgy Girl” 1966 from Georgy Girl, “The Look of Love” 1967 from Casino Royale, “Live and Let Die” (1973) from Live and Let Die, “Nobody Does it Better”(1977) from The Spy Who Loved Me, “9 to 5” (1980) from 9 to 5, “Papa Can You Hear Me” (1983) from Yentl, “Footloose” (1984) from Footloose, “Ghostbusters” (1984) from Ghostbusters, “The Power of Love” (1985) from Back to the Future, “Shakedown” (1987) from Beverly Hills Cop 2, “I Have Nothing” (1992) from The Bodyguard, “Save Me” (1999) from Magnolia, “Happy” (2013) from Despicable Me 2, “Can’t Stop the Feeling!”(2016) from Trolls, and “Mystery of Love” (2017) from Call Me By Your Name.

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My Top 5

Que Sera, Sera (Whatever Will Be, Will Be)—Doris Day

The Man Who Knew Too Much (1956) was a Hitchcock film I did not see until very recently. In fact, I had always associated the phrase “Que Sera, Sera” with high school girls that used to put it in the AIM away messages back in the day. I am a fairly cynical individual so the fatalistic message hidden in the happy-go-lucky song lyrics suit me quite well. Ironically, I used to hear this song as well and never associated it with that film until way later on, a testament to how much we all have yet to learn and connect in our lives.

Streets of Philadelphia—Bruce Springsteen

I like to think that Bob Dylan will never forgive The Boss for winning an Academy Award before him—given Dylan’s dabbling in filmmaking and penchant for having many artistic endeavors outside of music, painting, welding, motorcycle riding, etc.

All kidding aside, this song deserved the W in 1993 beating a Neil Young song written for the same film! That Neil Young song makes me cry every time at the end of the movie. It probably should have won. However, Springsteen’s song perfectly captures the emotion and tragedy of Tom Hanks’ plight during the film rather than as a coda. It’s a powerful film and one that directly addressed HIV/AIDS and homophobia by bringing the story to a mainstream audience.

Take My Breath Away—Berlin

The entire Top Gun soundtrack has always been a guilty pleasure of mine. Blasting down the road blaring “Danger Zone” by Kenny Loggins was one of my all-time greatest pastimes. This one makes the list because I am pretty sure my mom played it 1,000,000 when I was younger—I am pretty sure she still has it on rotation. Despite being born two years after this film came out, it was one of my favorites to watch when I was younger, mostly because I thought fighter planes were cool and the music was great. All of the various adult dynamics at play never really hit until I was into my teenage years.

The Weary Kind—Ryan Bingham

If there ever was a film I watched a lot, other than the next one, during my college years—it was Crazy Heart. This movie was some of Jeff Bridges’ best work since The Big Lebowski in my humble opinion. This song, partially written by T. Bone Burnett, who I personally don’t believe is a real person. I am pretty sure he is some sort of alien in a trench coat à la Men In Black. The dude’s fingerprints are all over every single earworm in recent memory. He came from another galaxy and brought us the magic to make magical tunes. Ryan Bingham’s performance of this song evokes that type of gut-wrenching bittersweet happiness that defines the ending of the film.

Things Have Changed—Bob Dylan

Rarely do two of my favorite things come together in a single creation. Michael Chabon sits on my Mt. Rushmore of authors. My Mt. Rushmore, by the way, not chiseled out of a mountain on stolen land. Bob Dylan, obviously, one of my greatest influences, both in music and writing. So when I first saw the film Wonder Boys after reading the book a couple of times, I was blown away. Here is a film that does not get the love it deserves, filmed in a city (Pittsburgh) I lived in for almost 10 years, pretty faithful to the source material in both story and dialogue, dark comedy with some over the top acerbic wit by nearly every actor and actress, and Bob Dylan wrote a song for it that won him an Oscar. ¹

Fun fact, if you look closely enough during the student assembly, you’ll see a young Rob McElhenney in what was probably his first role as a random student in a black turtleneck.

I’ll leave you with this music video that deserves its own Academy Award with Dylan lip-syncing and demonstrating his “unholy acting talent”² in the place of Professor Grady Tripp in various scenes from the film culminating with him munching on a burger in a western Pennsylvania diner parking lot. Absolute genius.

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Here is another shameless plug for subscriptions. Rather than go with a pay to read model, I switched to pay if you want. As an added incentive, other than the writing and supporting the Stack, I am giving away some sealed vinyl box sets and other ephemera worth exponentially more than the cost of a yearly subscription—read all about it here. As always, thanks for being here either way!

1. It should also be noted that Bob is so badass that he accepted the award from Australia because Neverending Tour means Neverending Tour.

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