What’s made this Yacht Rock journey so enjoyable? Is it the soothing waves of the ocean, the bellowing laughter of the man in the captain’s hat, or the dancing crew members as they form a conga line?

Those are all great, but let’s all admit that the music is what’s kept this party going. We’re only halfway there! Let’s continue with the Top 100 Yacht Rock songs of all time! Now pass me a margarita.

First, do you like the drawing of the yacht above? Of course you do – IT’S A FREAKING YACHT! And duh…this is a Yacht Rock countdown. Well, if you like illustrations of yachts, you’ll LOVE the work of Jess Perna, the creator of this and many other pretty fantastic things. Check out his stuff at jessperna.com and tell him I sent you. Then he hopefully won’t call me bad words anymore.

Next, check out 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

This journey is only half over! The Top 100 Yacht Rock Songs of all-time continues with #51-60:

60. “Sweet Freedom” – Michael McDonald

Yacht Rock legend and king of awesome beards, Michael McDonald, enters the countdown for his first – but definitely NOT his last – appearance with “Sweet Freedom” a hit song from the Running Scared movie.

Running Scared was another one of those 80s buddy cop movies, but the problem is that the “cops” were a tap dancer (Gregory Hines) and a stand-up comedian (Billy Crystal), so “Look out, crime!” apparently. No wonder they wanted to quit the police force and open a bar in Key West – they’re true Yacht Rockers at heart.

Hines and Crystal also starred in the music video, and while they were busy being totally hilarious and causing hijinks to ensue, Michael McDonald acts like he’s never been in front of camera before. Doesn’t matter though…his beard rules.

BEST TIME TO LISTEN TO THIS ON YOUR YACHT IS…

…once you outrun the five police boats who were on your tail.

BEST USE IN POP CULTURE

“Sweet Freedom” was also used as the theme song for the Yacht Rock internet series on Channel 101 because, duh.

BEST LYRIC

“Shine sweet freedom,
Shine your light on me.
You are the magic.
You’re right where I want to be!”

And where I want to be is anywhere near Michael McDonald’s beard.

59. “Key Largo” – Bertie Higgins

After Bertie Higgins failed to follow-up the success of his only hit “Key Largo,” he was plagued with personal and legal problems that included a divorce, heavy drinking, a night in jail for making threatening phone calls to the mother of his ex-wife’s boyfriend (huh?), and four months in prison for a 1995 DUI crash.

So it’s no wonder that the creepy music video basically features him taking some chick on a boat ride to Key Largo…against her will.

“Oh, I’m sorry…you didn’t know I was kidnapping you? My bad.” says Bertie Higgins.

BEST TIME TO LISTEN TO THIS ON YOUR YACHT IS…

…once you’ve slipped a roofie to all your fellow passengers before you drift off to a deserted island of your choice.

BEST USE IN POP CULTURE

The song was heavily inspired by the 1948 film Key Largo, which starred Humphrey Bogart and Lauren Bacall. However, in the film, Bogart and Bacall do not sail to Key Largo. Bogart arrives on a bus, and Bacall is already living there. So, nice research on that one, Bertie.

BEST LYRIC

“We had it all,
Just like Bogie and Bacall.
Starring in our old late, late show;
Sailing away to Key Largo.”

He must have written this during the heavy drinking part of his life.

58. “Easy (Like Sunday Morning)” – The Commodores

Just to be clear, “Easy” does not describe Lionel Richie’s girlfriend, but rather the calm, liberating feeling he has after their breakup. So no, it’s NOT a sweet love ballad; it’s about kicking some chick to the curb that Mr. Richie really didn’t like in the first place.

Richie says the phrase “Easy like Sunday morning” comes from living in a small Southern town, where all the action usually dies around 11:30 pm on Saturday night. So…while there is no such thing as late-night partying in the South, you can still legally marry your cousin.

Makes sense.

Listen to “Easy (Like Sunday Morning)” by The Commodores:

BEST TIME TO LISTEN TO THIS ON YOUR YACHT IS…

…during a casual Sunday morning cruise around the bay – probably right after brunch.

BEST USE IN POP CULTURE

“Easy” was included in an NFL promo during the 2000s featuring some loser who thought he was Eddie George. In it, he prepares for a football party with his buddies by mimicking George’s football moves. And by “mimicking” I mean acting like a moron. For example, the ad shows Eddie George taping-up before a game and then the “regular guy” taping-up the back of his TV remote.

This guy probably also thought he could become a military sniper because he was really good at Call of Duty.

BEST LYRIC

“Why in the world would anybody put chains on me?
I’ve paid my dues to make it.”

Sounds like a fantastic relationship.

57. “Heart Hotels” – Dan Fogelberg

No, this isn’t a velvet painting of Jesus walking around Miami Beach, but if it was you know it would be hanging in every room at a place called “Heart Hotels.”

Also, there’s no way “Heart Hotels” doesn’t have hourly rates. No way at all.

Listen to “Heart Hotels” by Dan Fogelberg:

BEST TIME TO LISTEN TO THIS ON YOUR YACHT IS…

…once all your passengers have checked in and been shown to their cabins.

BEST USE IN POP CULTURE

“Heart Hotels” was probably the inspiration for this scene from Dumb and Dumber, because, you know…the heart-shaped tub:

BEST LYRIC

“And the voices you hear at the top of the stairs,
Are only echoes of unanswered prayers,
echoes of unanswered prayers.”

If you’re staying at “Heart Hotels” then I promise you those voices have nothing to do with prayers.

56. “Margaritaville” – Jimmy Buffett

If you think the inspiration for “Margaritaville” came from Jimmy Buffet drinking margaritas all day, then you’d be partly right. He drank other things too, people. Nevertheless, this song quickly became the anthem for getting drunk at beach communities across the world.

Although Jimmy Buffet has never officially commented on the lyrics, there is general confusion as to whether he sings “Wasted away” or “Wastin’ away” in the chorus of the song. Does it really matter, though? I mean, the difference between getting wasted and being wasted is only a couple of drinks, right?

Listen to “Margaritaville” by Jimmy Buffet:

BEST TIME TO LISTEN TO THIS ON YOUR YACHT IS…

…just before you pass out and crash into the shore.

BEST USE IN POP CULTURE

Professional wrestlers Stone Cold Steve Austin and The Rock sang “Margaritaville” together on the November 12, 2001 episode of WWE RAW, which is strange because Stone Cold’s drink of choice is Budweiser.

Also, it would have been a challenge for the crowd to throw him margaritas instead of beer cans.

BEST LYRIC

“Wasted away again in Margaritaville,
Searchin’ for my lost shaker of salt.”

Or in Elvis’ case, a peanut butter and banana sandwich. Buffett revealed that “Margaritaville” was actually supposed to be recorded by Elvis Presley, but Elvis died the year that the song was released.

Or did he?????

55. “When I Need You” – Leo Sayer

Leo Sayer planned on having a casual jog along the shore, but how can someone think about exercise when the woman they love is miles away? So now all he can do is angrily throw rocks into the ocean, which actually reminded me of the time G.O.B. tried to do the same thing with a letter on Arrested Development.

But, I can’t really feel bad for Leo. I mean, why did he choose to go alone to come creepy, deserted theme park in the middle of winter?

Side note: My favorite part of this video is at the 2:10 mark when the two girls in the background suddenly realize they’re being filmed in a music video and run to get out of camera view. I can totally see the director yelling “GET THOSE GIRLS OUT OF THERE!!! LEO WANTS TO BE ALONE!!!!”

BEST TIME TO LISTEN TO THIS ON YOUR YACHT IS…

…when your about two hours from land and you realize you left your wife and children at the dock.

BEST USES IN POP CULTURE

Sayer performed “When I Need You” on The Muppet Show.

Except that bears CAN climb trees. I hope Leo’s friend gets there soon.

BEST LYRIC

“Miles and miles of empty space in between us.
The telephone can’t take the place of your smile.”

If only he could have used Facetime.

54. “Hold the Line” – Toto

Toto was one of the few American bands to make music videos before MTV was even on the air, so “TAKE THAT!” Michael Jackson and David Byrne. They moved on to create more elaborate videos in the 80s and became one of the most popular artists on early MTV.

So yes…this gem of a video ended up getting millions of views on YouTube, but sadly still not even close to the hits for Star Wars Kid or Rebecca Black’s “Friday.”

BEST TIME TO LISTEN TO THIS ON YOUR YACHT IS…

…when you’re over three hours late to your mother-in-law’s houseboat.

BEST USES IN POP CULTURE

This should probably be a “worst” but Mohegan Sun – one of the largest casinos in the United States – used “Hold The Line” in one of their commercials, but changed the words into some awful parody.

Hopefully, Toto never has to hear this ad, or that they have an open line of credit whenever they’re in Uncasville, Connecticut and want to play some blackjack.

BEST LYRIC

“It’s not in the way that you hold me.
It’s not in the way you say you care.
It’s not in the way you’ve been treating my friends.
It’s not in the way that you’ll stay till the end.”

It’s your body if we’re being honest. Oh…and your face.

53. “Mandolin Rain” – Bruce Hornsby

“Mandolin Rain” is about a failed romance between two people who enjoyed the rainfall and spent a lot of “intimate” time in it. And if this doesn’t sound like a complete movie cliché, then I don’t know what is.

Now that they have broken up, all he can do is think about her and cry every time it rains. Good thing he isn’t from Seattle.

BEST TIME TO LISTEN TO THIS ON YOUR YACHT IS…

…when you’re forced to stay in the harbor because of severe lightning warnings. Those are true tears.

BEST USES IN POP CULTURE

“Mandolin Rain” was used in the 2009 movie, Worlds Greatest Dad with Robin Williams. Hornsby made a cameo appearance in the film and played an alternate acoustic version of the song.

Fortunately, Hornsby and Williams did not share an intimate moment in the rain.

BEST LYRIC

“The song came and went,
Like the times that we spent
Hiding out from the rain under the carnival tent.”

Wait, you took her multiple times to the carnival? Of course you broke up.

52. “Who’s Crying Now” – Journey

“Who’s Crying Now?” Uhhhh, probably any girl who had to date a guy that looked like a member of Journey. Seriously, has there ever been an uglier band in the history of bands?

And notice I said “looked like” a member of Journey. If you’re actually dating a member of Journey then you can look past it because they’re millionaires and play music.

For women, it makes total sense, guys.

Listen to “Who’s Crying Now” by Journey:

BEST TIME TO LISTEN TO THIS ON YOUR YACHT IS…

…when you finally get back at your rival who wins the regatta race every year. Think of the 80s movie One Crazy Summer.

BEST USES IN POP CULTURE

“Who’s Crying Now?” was featured in the 2009 animated movie, Monsters vs. Aliens. And yes, even the monsters and aliens were better looking than Journey.

BEST LYRIC

“Two hearts, born to run.
Who’ll be the lonely one?
One love, who’s crying now?”

Looks aren’t everything, but they are something.

51. “Broken Wings” – Mr. Mister

You know that if your name is Mr. Mister, that at some point in your life you’ll be attacked by a hawk inside a church. You can count on it. You’re pretty much one step away from becoming the most interesting man in the world.

The video for “Broken Wings” is full of symbolism, and it should be. After all, the song was inspired by a 1912 novel that dealt with social and political issues in the Eastern Mediterranean.

Did you see the symbolism? He was driving a Thunderbird which then broke down because get it? Thunderbirds have wings, but then they’re “broken wings.”

Soooo deep, Mr. Mister.

BEST TIME TO LISTEN TO THIS ON YOUR YACHT IS…

…when you realize you dropped anchor just before putting your engine on full motor. Oops.

BEST USES IN POP CULTURE

“Broken Wings” was used as the background song for the awkward – but hilarious – love scene in MacGruber.

BEST LYRIC

“Take these broken wings,
And learn to fly again,
And learn to live so free.”

Except that they’re broken. But yes, please try to fly with those wings.

Check out 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