The top 100 yacht rock songs of all time 21-30

Top 100 Yacht Rock Songs – #21-30

For those of you who thought the Top 100 Yacht Rock songs of all time countdown was “dead in the water,” this is for you. And no, I will not pardon that pun.

You’ve been able to see the harbor in the distance for quite some time now, but you never seem to get closer to shore. Well…that’s all about the change. Rev that engine back up, take down the sail and throw your captain’s hat back on, because we’re on our way home!

See, I promised I’d get you all back safe.

Did you miss out on the other editions of the TOP 100 YACHT ROCK SONGS? Read them all here!

Top 100 Yacht Rock Songs – #91-100
Top 100 Yacht Rock Songs – #81-90
Top 100 Yacht Rock Songs – #71-80
Top 100 Yacht Rock Songs – #61-70
Top 100 Yacht Rock Songs – #51-60
Top 100 Yacht Rock Songs – #41-50
Top 100 Yacht Rock Songs – #31-40
Top 100 Yacht Rock Songs – #21-30

The Top 100 Yacht Rock Songs of all-time continues with #21-30:

30. “Hey Nineteen” – Steely Dan

Steely Dan "Hey Nineteen" is in the top 100 yacht rock songs of all time.

It’s hard to fathom how a middle-aged man could be disappointed with his young, 19-year old girlfriend, particularly when he looks like a member of Steely Dan. If anything, it’s her parents that should be disappointed, because their daughter is dating a guy who either resembles a level 100 Dungeons and Dragons player, or a guy who probably definitely smuggles cocaine for a living.

Well, at least Steely Dan co-founder Donald Fagen was up front about their intentions with “Hey Nineteen,” but it doesn’t make it less creepy.

“I hope songs like ‘Hey Nineteen’ would be enjoyed by soccer moms in dentist chairs bobbing their heads, unaware of the filthy lyrics.” – Donald Fagen

Alrighty, then.

I guess now my daughter can’t date until she’s 40.

Listen to “Hey Nineteen” by Steely Dan:

Steely Dan - Hey Nineteen - HQ Audio

…when you’re “forced” to take your daughter’s sorority for a cruise around the bay for their island themed party.


In the “Fall” episode of Gilmore Girls: A Year in the Life, Luke and Lorelai plan to surprise each other with a flash mob performance for their wedding. Luke chooses Hey Nineteen,” which Lorelai refers to as “old, boring, man music.”

“What does your flash mob do? Jump out, lose their hair, complain about their backs, and doze off?” – Lorelei Gilmore

Sorry if that upsets Steely Dan, but they should just be grateful they didn’t write this song about Rory’s best friend, Lane. Let’s just say her mom wouldn’t laugh about it.


“Hey Nineteen,
That’s ‘Retha Franklin.
She don’t remember the Queen of Soul.”

In the song, the older man is frustrated because the 19-year old doesn’t even know who Aretha Franklin is. That would be the modern-day equivalent of me dating some college chick who had never heard of the former Queen of Pop, Madonna.

Ok, that’s probably a good thing.

29. “Dreams” – Fleetwood Mac

Fleetwood Mac "Dreams" is in the top 100 yacht rock songs of all time.

The crazy, tumultuous relationships of the Fleetwood Mac band members have been well documented, but at least when Stevie Nicks wrote the lyrics to “Dreams” she had good intentions.

During the recording sessions for their Rumours album, everyone in the band was going through “some thangs” with their personal lives: Stevie Nicks with Lindsey Buckingham, John McVie with his wife Christine, and Mick Fleetwood with his wife Jenny Boyd.

Oh, and they were all doing a TON of drugs. One could say it was an era of “peak Fleetwood.”

Ironically, Rumours was their most successful album, even though most of the songwriting was on an individual basis and they pretty much hated each other. Stevie Nicks wrote “Dreams” about Lindsay Buckingham as an invitation for him to leave their relationship. Instead of just a normal, “yeah, let’s just be friends” from Lindsay, he responded with the now famous song “Go Your Own Way,” which was basically the same song as “Dreams,” but times 100 on the rudeness scale.

Also, it was their only U.S. number one single. That’s sooooo Fleetwood.

Listen to “Dreams” by Fleetwood Mac:

Fleetwood Mac - Dreams [with lyrics]

…when you break up with your fiancé and she responds by setting your yacht on fire.


Will and April sing “Dreams” to their students to introduce the Fleetwood Mac-themed episode of Glee appropriately titled “Rumours.”


It’s the one where Brittany starts her own gossip internet talk show, Kurt is possibly cheating on Blaine with the fish-mouthed Sam, and Santana worries about coming out as a lesbian.

You know…normal high school stuff.


“Thunder only happens when it’s raining.
Players only love you when they’re playing.”

False. Players NEVER love you. That’s why they’re players.

28. “All Right” – Christopher Cross

Christopher Cross "All Right" is in the top 100 yacht rock songs of all time.

“All Right” is probably how Christopher Cross felt after only achieving a Gold Certification for his sophomore album, Another Page. But can you blame him? His self-titled debut album went five times Platinum and won five Grammy Awards, including Album of the Year, Song of the Year, and Best New Artist.

So yeah…Gold “sucks” by Christopher Cross standards.

“All Right” even features Michael McDonald on background vocals. That alone should make it a top Yacht Rock hit. But don’t worry…we’ll probably see more of Mr. Cross as we reach the Top 20.

Listen to “All Right” by Christopher Cross:

Christopher Cross - All Right (1983) //Good Audio Quality\

…when you discover a hole in side of the hull and you’re still miles from shore.


“All Right” was used in the montage that CBS used for its coverage of the 1983 NCAA Men’s Division I Basketball Tournament.

CBS NCAA 1983 "Pre" One Shining Moment


The tournament highlights featured the iconic shot of NC State’s Jim Valvano running up and down the court after their last second championship win over Houston. However, the runner-up could easily go to some cheerleader taking a charge at the 1:12 mark from North Carolina’s Joe Wolf.

She probably dissed Michael Jordan.


“‘Cause it’s all right.
I think we’re gonna make it.
I think it might just work out this time.”

I think MTV had something to say about that.

27. “Baker Street” – Gerry Rafferty

Gerry Rafferty "Baker Street" is in the top 100 yacht rock songs of all time.

In the late 1970s, Gerry Rafferty was a prisoner to his own music. He was involved in a huge legal battle with his former band, Stealers Wheel, and was not allowed to release any of his own material due to the band’s recording obligations.

The good news is that it gave him TONS of time to write songs. In fact, Gerry wrote “Baker Street” while staying at his bro’s flat in London while waiting to meet with his lawyers. And yep, you guessed it…his mate lived on Baker Street.

Baker Street is famously known as the home of the fictional detective, Sherlock Holmes, but it’s no “mystery” what really made this song famous: THE SAX. The song features a prominent eight-bar saxophone riff played by session musician Raphael Ravenscroft. He just happened to be in the studio that day, and Gerry suggested that he record the break using the alto saxophone he had in his car. This famous riff became known as “the ‘Baker Street’ phenomenon” and a resurgence in saxophone sales and their use in mainstream pop music and advertising.

Unfortunately, Ravenscroft later revealed that the sax was out of tune during the recording, and was pretty pissed when he heard it in the final track.

Yeah, I don’t think Gerry minded at all. It was rumored he made around £80,000 (about $97,000) per year from the song.

Listen to “Baker Street” by Gerry Rafferty:

Gerry Rafferty - Baker Street (UK)

…when you barely escape an island full of cannibals and sail off into the sunset.


This one’s a tie.

In the closing scene of the popular Simpsons episode “Lisa’s Sax,” Lisa performs the “Baker Street” sax hook while she sits with Homer in the hospital during his coma. I assume it was caused by donuts.

Lisa sax solo "baker street" (simpsons version)


“Baker Street’s” saxophone line is featured numerous times in the Rick and Morty episode “M. Night Shaym-Aliens!”

Rick and Morty - They Blew Up


“When you wake up it’s a new morning.
The sun is shining, it’s a new morning.
You’re going, you’re going home.”

I assume this was in reference to the end of Rafferty’s legal and financial frustrations with his former band, but it could also be what his friend thought when Gerry finally left his London loft.

26. “You’re The Only Woman (You And I)” – Ambrosia

Ambrosia "You're the Only Woman (You and I) is in the top 100 yacht rock songs of all time.

“You’re the Only Woman (You & I)” was Ambrosia’s last hit song, reaching No. 13 on the Billboard 100. The album One Eighty earned them three Grammy nominations, including Best Pop Vocal Group. Many fans thought the title of the album was a nod to the group’s “180-degree” change in music direction. They had already began to move away from their calm, lush arrangements and introduced a more upbeat, aggressive jazz style. Think of going from listening to music you’d hear in the lobby of a dentist’s office to music you’d hear in the waiting area of a hair salon.

HUGE changes for Ambrosia.

Well, this had already pissed off  the group’s keyboardist, Christopher North, who left the group in 1977 over creative differences. Ironically, that was the exact start of the band’s commercial success.

HUGE mistake for Mr. North.

Listen to “You’re The Only Woman (You And I)” by Ambrosia:

Ambrosia - You're The Only Woman

…when you make a promise to never wear your grandfather’s prized captain’s hat and end up losing it in the ocean during a wind storm.


Ambrosia is very protective of their songs, so this might actually be the WORST use. A terrible group called “The Brat Pack” (no, not that one) did a cover to “You’re The Only Woman (You And I)” in an effort to increase their pop appeal. They probably figured “Hey, it worked for Ambrosia, it will totally work for us too!” but forgot that they completely sucked and Ambrosia doesn’t.

The Brat Pack - You're The Only Woman(1990)


“‘I know you’re the only woman that I’m dreamin’ of.
You’re the only woman that I really love.”

Says the guy who never remembers his dreams and who apparently tells multiple women he loves them.

25. “Shadow Captain” – Crosby, Stills & Nash

"Shadow Captian" by Crosby, Stills and Nash is in the top 100 yacht rock songs of all time.

Aside from also being an awesome pro wrestler name, “Shadow Captain” is one of several songs that David Crosby wrote after waking up in the middle of the night. Kind of makes you wonder if he wrote this in the middle of the day if it would be just called “Captain.”

Nevertheless, it begs the question: what exactly is a “Shadow Captain?”

Well, if you’re a Star Wars fan you already know the answer. The Shadow Captain was a male Imperial Commando who served the Sith Empire during the Cold War as a member of the elite shadow commandos. And yes…I TOTALLY had to look that up.

"Shadow Captain" by Crosby, Stills and Nash is in the top 100 yacht rock songs of all time.

For you literary types, you know Shadow Captain as part two of the Overfiend sci-fi novel series by author David Annandale. In this book, Raven Guard Shadow Captain Krevaan forms a fragile alliance with the mysterious eldar, and prepares to make a decisive strike against the orks that may win the day on Lepidus Pri…

Ok, this conversation got REALLY dorky, really fast.

Listen to “Shadow Captain” by Crosby, Stills & Nash

CSN - Shadow Captain

…when you’re smuggling in a stolen shipment of VCRs at three in the morning and don’t want to attract attention.


I think we can all agree that I’ve already said enough about Shadow Captains for one day.


“Oh, captain, why these speechless seas
That never seem to land?
Oh I need to understand.
Could a little light be that bad?”

Dark and quiet, just how Shadow Captains like it.

24. “Eye In The Sky” – Alan Parsons Project

Alan Parsons Project Eye in the Sky is in the top 100 yacht rock songs of all time.

Many have speculated about the meaning of “Eye in the Sky,” but the most popular opinion about its origins reads more like a conspiracy theory.

The idea is that the “eye in the sky” is borrowed from George Orwell’s book 1984. However, aside from the song’s title, there’s really nothing else in the song to support that reasoning. That’s like saying Chumbawumba’s song “Tubthumping” is about, well…thumping tubs. That’s not only a terrible theory, but it’s also an equally terrible song.

Some think the song describes the bitterness following the end of a relationship, but when you spend your time watching your ex’s every move and trying to read their mind then that’s not common heartbreak – that’s stalking.

No, in fact “Eye in the Sky” is about one thing: GAMBLING.

Vocalist and co-writer Eric Woolfson loved spending time in Las Vegas and was fascinated by the hidden cameras that were watching his every move. Maybe that’s why their previous album was named The Turn of a Friendly Card.

Listen to “Eye in the Sky” by Alan Parsons Project

The Alan Parsons Project- Eye in the Sky

…when you discover the peephole someone carved into the wall of the girls’ cabin dressing room.


“Eye in the Sky” was used as background music in the movie Edge of Seventeen when Nadine confronts Krista about catching her sleeping with her brother Darian the night before. I bet her eyes in the sky were burning.

Alan Parsons Project Eye in the Sky is in the top 100 yacht rock songs of all time and is featured in the Edge of Seventeen movie.


“I am the maker of rules,
Dealing with fools.
I can cheat you blind.”

Remember Eric: ALWAYS double down on 11.

23. “Thunder Island” – Jay Ferguson

Jay Ferguson Thunder Island is in the top 100 yacht rock songs of all time.

What do you do when you’re trapped on a deserted island with some one who looks like a cross between watermelon-smashing comedian Gallagher and Desmond from LOST?

You do what anyone else would do: Pray for thunder…and lightning….and maybe a tidal wave. Those are the only things that are going to put you out of your misery on this island.

Now, don’t confuse “Thunder Island” with “Thunder in Paradise.” No, “Thunder in Paradise” is a happy place with bikini models and Hulk Hogan.

Listen to “Thunder Island” by Jay Ferguson

Jay Ferguson - Thunder Island (CD Audio Quality)

…when the dark clouds roll in over the ocean and you’re not sure if you’ll make it back to shore.


“Thunder Island” appears in Anchorman 2: The Legend Continues during the awesome RV crash scene. Just let it run on cruise control.

Anchorman 2- hilarious RV scene


Side note: You also get a bonus Yacht Rock gem “Muskrat Love” during the part where their cruise control fails.


“She was the color of the Indian summer.
And we shared the hours without number.”

I believe it’s “Native American summer,” Jay.

22. “Dancing in the Moonlight” – King Harvest

King Harvest "Dancing in the Moonlight" is in the top 100 yacht rock songs of all time.

“Dancing in the Moonlight” is supposed to be a song that describes a place of joy and harmony where everyone gets along, but it’s origins are the exact opposite.

Keyboard player and songwriter Sherman Kelly wrote the song after a trip to Saint Croix in the Caribbean, where he was attacked by natives and left for dead.

“I envisioned an alternate reality. The dream of a peaceful and joyful celebration of life.” – Kelly, on writing the song while recovering in the hospital

And if that isn’t the most Yacht Rock thing ever then I don’t know what is.

Listen to “Dancing in the Moonlight” by King Harvest

Dancing In the Moonlight

…when you host your company party for a river cruise and you get to dance with that attractive coworker you’ve had your eye on.


Hanes used “Dancing in the Moonlight” for a creepy underwear ad where a girl watches her mom jump on a trampoline in just her bra and panties. I can’t stress enough how much I REALLY hope that’s her mom.

In 1994, the (horrible) Baha Men covered “Dancing in the Moonlight” for that (equally horrible) Fat Albert movie. Yet, somehow that was worse than watching that mom trampoline in her underwear in front of her daughter.


“Everybody here is out of sight.
They don’t bark, and they don’t bite.
They keep things loose, they keep things light.”

Hey, why don’t I just go eat some hay, make things out of clay, lay by the bay? I just may! What’d ya say?

21. “Kokomo” – The Beach Boys

Kokomo by the Beach Boys is in the top 100 yacht rock songs of all time.

The most intriguing thing about “Kokomo” is that it’s not even a real place. Well…at least it didn’t used to be a real place until the song became popular. Ok, actually it was a real place, but not in the way you think. I’ll explain…

There are actually several “Kokomos” around the world, but they are mostly cities in places that you probably don’t want to visit. For example, Kokomo, Colorado is literally a ghost town; Kokomo, Texas was ravaged by a wildfire in 2005; and Kokomo, Indiana used to host record-setting Ku Klux Klan rallies in the 1920s.

“Let’s just say no one’s going to work on their tan in Kokomo, Indiana since they’re all very afraid of a little color.” – comedians

The fictional island of “Kokomo” in the song was supposed to represent all the tropical places people think of when wishing to escape their dreary daily life. The Beach Boys released “Kokomo” to very little fanfare in July 1988, but it did not become a huge hit until the movie Cocktail came out a few months later. That’s when it put The Beach Boys BACK on the map, and the actual island of Kokomo ON the map.

Sandals Royal Caribbean wasted no time in capitalizing on the song and created a small resort named “Kokomo Island” off the Florida Keys (get it…just like the lyrics). Since this time, numerous Caribbean-area businesses involved in the tourist industry have cashed in on the popularity of “Kokomo” by naming bars, hotels, and casinos after it.

To be honest, having John Stamos and Tom Cruise in the mix didn’t hurt either. You wouldn’t be out of line by calling them Kokomo’s “founding fathers.”

Listen to “Kokomo” by The Beach Boys

Kokomo - The Beach Boys 1988 (Retro Web)

…when it’s your turn to wash the boat, BUT it’s also a 4-day weekend…sooooooooooo.

“Kokomo” was included on the Cocktail movie soundtrack, which featured Tom Cruise flipping bottles and pouring drinks in Jamaica. Ted Mosby and Barney Stinson tried to emulate Mr. Cruise on “How I Met Your Mother” when Carl lets them watch MacLaren’s bar for an evening. I think they owe Carl some alcohol.

“We’ll put out to sea and we’ll perfect our chemistry,
And by and by we’ll defy a little bit of gravity.
Afternoon delight, cocktails and moonlit nights,
That dreamy look in your eye, give me a tropical contact high.”

Between the “afternoon delights” and “contact highs” Kokomo actually sounds more like a “sexy” Jamaica.

Check out the other editions of the TOP 100 YACHT ROCK SONGS OF ALL-TIME:

Top 100 Yacht Rock Songs – #91-100
Top 100 Yacht Rock Songs – #81-90
Top 100 Yacht Rock Songs – #71-80
Top 100 Yacht Rock Songs – #61-70
Top 100 Yacht Rock Songs – #51-60
Top 100 Yacht Rock Songs – #41-50
Top 100 Yacht Rock Songs – #31-40
Top 100 Yacht Rock Songs – #21-30

If you love Yacht Rock, then check out Hello, Loser on Facebook or follow me on Twitter.

26 thoughts on “Top 100 Yacht Rock Songs – #21-30”

  1. THANK YOU, THANK YOU, THANK YOU for the update!!! I grew up in the era of peak Yacht Rock, but it took me stumbling on this list awhile back to really remind me of why I loved it so much. Nowadays, I drop “guilty” when I describe it as a pleasure.

    I’m also going to see a Yacht cover band next month, have changed my Facebook profile picture to one with a Captain’s hat, pipe, and Navy blazer, and evangelize about the music whenever someone asks me about it. I’m sure this is all incidental, however.

    Also: “Thunder Island” is the song I think of when I think of Yacht Rock even more so than “Brandy,” “Sailing,” “Key Largo” or “The Piña Colada Song.” So thanks for including it.


  2. Great to see this back! A pleasure, as always. I should warn you though, since those innocent days of 2013, the discussion around yacht rock has gotten very academic. The “Beyond Yacht Rock” podcast, especially, has drilled deep into the genre, so the criteria for what is/isn’t yacht rock is pretty specific at this point.

    So don’t be surprised is you get a bunch of comments declaring some of your songs “nyacht.” But pay them no mind—keep doing what you’re doing. Sail on, brother.

  3. Thank you for the update to the list! ?? I’ve been following your Top 100 Yacht Rock list for years. I check back every few months or so. So, imagine my glee when I saw your latest addition. ?

    I have a Yacht Rock playlist with over 170 songs on it. In addition to being greatly entertained by your commentary on each song, I also utilize your updates to see if I’m missing any tunes that I need on my Yacht Rock playlist. I was happy to make three new additions with your latest update — “Eye in the Sky”, “You’re The Only Woman (You And I)”, and “Shadow Captain”. Thank you.

    Can’t wait for the final 20! ?

    Excellent stuff. ??

    [Btw, I noticed a couple typos, if you’d like to correct: 1) I think the word “be” is missing from “Ambrosia is very protective of their songs, so this might actually the WORST use.” 2) The 2nd “that” should be “than” in “Yet, somehow that was worse that watching that mom trampoline in her underwear in front of her daughter.”]

      1. I’ve got a Yacht Rock Playlist on Spotify and this list has gotten it up to 170+ total!
        Need that Top 20.

      2. We are being patient but come on man…….!

        Probably time to bring this “ship into the shore”….we need your finale!


        ….great entertainment btw. I just re-did your 100 to 21 and it never gets old.

        1. Ahoy matey! Yacht rock fan over here -*waves wildly. I’ve been following this blog and waiting years for the final top 20. Please update this soon Thank you!!

  4. Perhaps it’s best that this yacht never heads in to the harbour. Drifting eternally on the calm ocean waters until a strong wind hits the sail, forever accompanied by the smooth sounds of yacht rock with the dedicated followers of this epic journey free to choose the course in their own minds and playlists.

Talk to me, loser.

This site uses Akismet to reduce spam. Learn how your comment data is processed.