Lilly Winwood in The Waiting Room

Patience is a virtue as Lilly Winwood drops a surprise covers EP.

I first started listening to her song Sleep Issues in February, and quickly became Lilly Winwood’s No. 1 fan in England. I’m still playing it, and I have all of the music she has recorded in the last few years, including her Bandcamp album Time Well Spent. Lilly has been releasing a cover song or two throughout the summer and she recently dropped a surprise covers EP called The Waiting Room.

lillywinwood

A post shared by @lillywinwood

In the post above, Lilly proudly introduces her new release in her own lovely and engaging style:-

consider this EP a moment between chapters - a small offering while i work on my LP of originals set for release next year ❤️ my hope with these songs is to honor the artists that really shaped my influence - The Allman Brothers, Aretha, Bob Dylan, Feist, my father even, but also to point toward a shiny new groovy musical phase which I hope keeps ya excited til the next round comes✨ thanks for listening guys sincerely

I take from this that Lilly considers this EP a pause between releasing her own original albums. But we fans always love a cover song, a reworking of something familiar and comforting. One incidental point is that I had not heard a single one of these songs before, which perhaps says more about my limited musical landscape than I would ordinarily admit.

always singin’

A cover song gives the listeners some room, and puts the singer in a different light. I imagine it’s something like adapting a novel into a screenplay: you have all the parts in front of you, and it’s just a case of chipping your version of the story out of the stone of the book.

You will recognise all of these versions as being innately Lilly Winwood songs. She has re-interpreted them, changed them, improved them possibly, made them fresh again. She has certainly re-imagined them for a new generation of listeners.

One of the things that most appealed to me about Lilly’s songs was always the lyrics. I get a sense of how important the words are to her, especially in her more autobiographical songs like Laundry Day, for example. This is how she has described her music previously:-

“It’s exciting,” Winwood says, speaking not just of her latest project, but also the musical passion encoded in her DNA. An eclectic fusion of trans-Atlantic roots-music styles, hers is an unpredictable sound of opposing forces, with its feet firmly on the ground and head in the clouds – quite literally.

I have been listening to another huge talent this year, Screamer’s Madaline Collins, who let this little gem slip one day:-

“I’ve seen Lilly Winwood here in Memphis twice but this was years ago… she will move you to tears that one.”

If there is one phrase I can think of to explain Lilly’s appeal it is this: something you got. She’s just got that little something special that makes all the difference. Let’s take a closer look.

The Waiting Room Track by Track

Had To Cry Today (Blind Faith)

This is a real belter to kick us off, slightly grungy with a strong groove. Whenever I write about Lilly, I have a little post-it note that says “don’t mention Steve” and there are a couple of reasons for this. The most important reason is that Lilly is a stand-out talent, an individual in her own right, and I had made an assumption I now consider false, that she might have grown tired of being associated too closely with her father. As if to prove me wrong, she is touring throughout September with Steve. Indeed they have a show this very evening.

Lilly has achieved all of her success because of who she is. It’s clear in her lyrics about waiting tables and working long hours to support her music. Her inclusion of Blind Faith’s Had To Cry Today, originally released to coincide with Steve’s birthday, shows how proud she is of her family. This is a really touching, sad song, sung so beautifully.

Let It Die (Feist)

A slower song, sad in a different way, wistful. It builds up the the following verse which is so subtle and true and deep, and worth noting:-

The saddest part of a broken heart
Isn't the ending so much as the start
The tragedy starts from the very first spark
Losing your mind for the sake of your heart

Something You Got (Wilson Pickett)

One of three songs that were released in the spring, this is a very simple song with a killer vocal. The tune this time is really happy, hip, groovy, quite light. But I feel sadness this time too.

I have seen this ability before that Lilly has of taking a light, boppy tune and then layering it with so much emotion with her voice. I can’t offhand recall a song of hers that is out-and-out lightweight, funny, happy. I always feel there is some note of sadness around the corner, just like in real life.

Tonight I’ll Be Staying Here With You (Bob Dylan)

This was the first single Lilly released back on March 14, and it was around the time I first started writing my music profiles. The first profile I ever wrote was the Lilly one, which you can read below.

It is always interesting when a song written and sung by a man is given a new perspective by a female singer, and this lesser known (to me anyway) Dylan song was a wonderful start to the spring.

Wasted Words (The Allman Brothers)

This is my initial favourite on the EP, perhaps because it hadn’t been released earlier in the year so it has a freshness. It is the least sad, perhaps the loudest, although there is a lot of volume in this collection. Could this be the best Christmas blues song of all time? It’s sassy, with a harmonica and a lot of ‘tude.

Well, I ain't no saint and you sure as hell ain't no savior
Every other Christmas I would practice good behavior
That was then, this is now
Don't ask me to be Mister Clean
'Cause baby, I don't know how

Baby I Love You (Aretha Franklin)

A tranquil, soothing end to a killer set of tracks. A real jam. Many of these tracks have a crackling, dry quality. They were all recorded at the same time, with more or less the same cast, and I think it shows. What Lilly Winwood has achieved here, with a set of cover songs no less, is to give the welcome impression that these are six original Lilly Winwood songs. Bravo.

What this collection shows clearly is what a student Lilly is of her ancestors, both literally and musically. I have learned this year not to pigeonhole or label musicians, especially when they have such a broad range of influences and styles as Lilly does.

In these six songs we have bluesy Lilly, a musician’s musician, jamming her way through some of her favourite tunes with some of her favourite people. One thing this EP is not is any sort of placeholder. It genuinely stands on its own.

This is where Tennessee Vibes began back in February 2025, see below. One of the things that music can do is make unexpected connections. It leads you to think you know someone you have never met. You know the name of their dogs (one of them is mushu) and you see their holiday photos, a very American lake if I recall. I know more about Lilly Winwood than I do about most of my actual colleagues, and many of my friends come to think of it. Such is the power of music but also one of the overlooked benefits of social media.

You can follow Lilly in all the usual places including on Instagram, TikTok and on her own website. You can book tickets to see her with Steve Winwood in September.