OOPS! 50 of 2025: #25-21: A Grammy Winner, A Country Singer and a Lonely Drifter

I think that this section above all others will ahve you questioning how I get to do a podcast about music. You will openly question my listening skills when you realise that these songs were not on the top 50. What can I say??? Sometimes your guy just misses the mark. But, I’m big enough to admit that I’m wrong and the OOPS! list is my opportunity to make things right. So, let’s get into my shame.

25. Olivia Dean: Man I Need

Yes…somehow the woman who dominated the charts and won a Grammy missed out on the to 50. What can I say…I was late to the party…but I’m glad I made it. Jazzy and soulful vocals wrapped around expert hooks and tight pop arrangments…what’s not to like. She reminds me a little of Feist in how the vocal is a little jazz, a little soul and a little pop. I could listen to Olivia Dean all day and this is only the beginning of her wonderful career.

24. Charlie Crocket: Lonesome Drifter

I have written about Charlie in the past for Black History Month posts and he has featured on past top 50s. I love what he is doing to country by opening it up with more of a modern flare and songs with more depth than drinking and driving a truck….I’m looking at you Post Malone…be better. Even though Charlie harkens back to the country of old school Willie Nelson and Charley Pride, there is a freshness to it that I really love.

23. Caroline ft. Caroline Polachek: Tell me I Never Knew That

Experimental. Beautiful. Organic. Fragile. These are all words that come to mind when I hear the indie masterpiece with one of the biggest indie super duos in the band Caroline and Caroline Polachek. Each of these artists have made either the Top 50 or OOPS! list in the past individually, but somehow this pairing missed my radar this year. The track itself is a journey to listen to and moves to a variety of places and reminds me of the experimental side of Neutral Milk Hotel. Just a wonderful piece that needs to be experienced.

22. Cardi B: Bodega Baddie

I’m not sure how I missed this. For some reason I think that Cardi B puts out music all the time, but this is her first record in like 7 years. I think that she features on so many singles that make my Top 50 lists that I can overlook her. Well shame on me. This is Cardi how you want…sexual, powerful, grunting, rolling her Rs to an inch of their lives and bringing all the attitude. You add in some Spanish and salsa music…you got a banger.

21. Monte Booker ft. Mereba: b 2 b

Monte Booker bring some experimental electro beats to this track, much like how Robert Glasper brings experimental modern jazz to hip hop tracks. Complete with distortion and fragmented beats, you feel like you are listening to some DIY track in your arty friend’s house. Mereba’s tight bars and soulful vocal really takes these raw beats to another level and makes the song. I love how the track hovers between raw hip hop and totally falling apart…it inhibits this sonic grey area that I really love.

It’s time. The top 20. I don’t want to spoil anything, so no more clever hints…you will just have to wait and see…..