In the early Eighties, Michael McDonald was such an omnipresent force in the music industry that he inspired one of the greatest sketches on SCTV. It stars a bearded Rick Moranis as McDonald, who frantically parks his vehicle at a studio and comically races in and out of the room just in time to sing backing vocals on Christopher Cross’ “Ride Like the Wind.” His signature voice — those immeasurably deep, blissful pipes — echo through the control room.
The zany sketch was grounded in truth, since McDonald was indeed absurdly busy when it aired, juggling his commitments to the Doobie Brothers, guest spots with Steely Dan, James Ingram, Kenny Loggins, and more, and cutting songs for his 1982 debut solo LP, If That’s What It Takes. Throughout the decades after that, McDonald never really left the pop cultural landscape. The sketches continued, with McDonald even joining in on the joke. In 2005’s The 40-Year-Old Virgin, electronic store employee Paul Rudd explodes on his boss, Jane Lynch, about “Yah Mo B There” incessantly playing on the television sets. “If I hear ‘Yah Mo B There’ one more time, I’m going to yah mo burn this place to the ground,” he tells her.
Talking about the Judd Apatow film now, McDonald answers with a typically chill, level-headed response: “I have to be honest, I thought it was hysterical,” he says. “When you get to a certain point in your career and your music becomes less relevant, your pathetic comic value might come in handy. And that was that moment for me. Paul Rudd actually stopped me in the airport, and we were both rushing to different flights. And he goes, ‘I hope you weren’t offended by my performance in The 40-Year-Old Virgin.’ And I said, ‘Absolutely not. It was great. I still laugh about it when I think about it.’”
McDonald, whom Rolling Stone once described as a man who “could sing the New York telephone book and break your heart,” has had quite a busy year in 2024. The yacht rock legend recently released his excellent memoir, What a Fool Believes, co-written with Paul Reiser, and he’s back on the road with the Doobie Brothers, celebrating the band’s 50th anniversary. (He also reveals there’s a new Doobies album on the way.) And on Friday, he’ll appear in HBO’s Yacht Rock: A Dockumentary, which traces the history and legacy of the genre.
With all of these retrospective projects, compiling a list of key songs in his career was no sweat. “It took me a minute, because I wanted to make sure they had some meaning to my gradual evolution as a person,” McDonald tells us on a recent morning over Zoom, holding a cup of coffee in his Santa Barbara home. “It’s funny. It’s all gone by so quickly. When we talk about things that seem like yesterday, we realize that 30 years goes by in a flash if you’re not careful.”
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Mike McDonald, ‘God Knows’ (1971)
It wasn’t the first recording I’d ever done — not even the first professional recording I’d done — but it was really the beginning, where I thought that I would do this as a real occupation. Back in St. Louis, when you made a record there, you were bucking the odds that anyone would ever hear it. You knew that going in. If you were lucky enough to get on a local radio station, somebody might be fooled into thinking you actually had a hit song on the radio, but it wasn’t really meaningful except in a very regional way. And I’d had that experience. But coming to L.A. and working with [producer] Rick Jarrard, who was at the top of his career accomplishments with having done Harry Nilsson’s Aerial Ballet, José Feliciano’s “Light My Fire,” and Surrealistic Pillow by Jefferson Airplane — I felt like, “Oh my gosh, it doesn’t get any better than this.”
It was all very surreal. I went from playing crappy little dives all around the Midwest with my buddies. Most of us dropped out of high school to do this full-time, and we were barreling down the highway to some gig already late in a van that could break down at any moment — one of us had to lay on top of the gear because there wasn’t enough room for everybody. We loved what we did, but it was a different reality. And then all of a sudden I’m in L.A., and I’m this 19-year-old kid people are putting a little bit of interest and faith in. I cut this song and RCA liked it and signed me as an artist. I’m sure I signed away my firstborn on that contract, but I would’ve done anything just to stay out in California and make records.
Rick Jarrard was kind enough to use me on his other sessions. Really just an effort to try to keep me alive out there. So that kept me going for a while. And somehow from that I transitioned into … a shit show with my life. I went from making a whole album for RCA Records to pretty much being the guy who drove down and brought cocaine to the horn section. I suddenly started to realize, “Oh, this is how things go to hell in a hand basket if you let them.” When I look back, that song packs a lot of memories — sweet and bitter — for me.
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Steely Dan, ‘Bad Sneakers’ (1975)
Timothy B. Schmit and I were cut from the same cloth. He made me laugh once. He goes, “It was always the same drill. You got this great gig, that gig you’ve been waiting for, and then the band breaks up a month later.” And that’s what happened to me with Steely Dan. All of a sudden I went from playing bars in Glendale to touring the United States and Europe with Steely Dan. The pay wasn’t much, believe me. But nobody got rich in Steely Dan at that time — not even Donald [Fagen] and Walter [Becker]. It was really putting your shoulder to the wheel and going out and doing the grind. I was in heaven. It was my favorite band at the time.
Came home from all of that, only to find out that Donald and Walter had decided to disband the whole thing and just stay in the studio and make records and never tour again. I should have known the other shoe was going to drop. I was just grateful to have had the experience up to that point.
So I was pleasantly surprised when Donald and Walter reached out to me to come and work on the next record they were doing [Katy Lied]. “Bad Sneakers” was the first track that I ever recorded in the studio with Steely Dan as a background singer. It was an opportunity for me to use my voice almost like a singular instrument. I was doing all the parts and doubling them. I had done that on demos of my own because I couldn’t afford to hire singers, but I never really thought much about it. Donald was experimenting with the sound of my voice in ways that I hadn’t even thought of. I think we all knew that Donald and Walter were capable of almost anything. We knew they were onto something that hadn’t been done before. For me, it was a pretty heady thrill to be part of the sound of Steely Dan.
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Doobie Brothers, ‘Takin’ It to the Streets’ (1976)
I got the gig with the Doobies through Jeff Baxter, who I had been in Steely Dan with. We got to be friends. Jeff recommended me for this emergency situation where Tom [Johnston] had some medical issues, and he had to come off the road. They would tour for six months straight, all over the globe. They had a lot of gigs booked, and they didn’t want to cancel. They had enough guitar players to pull it off, but they needed someone to sing some of the songs. And they wanted to bring in a keyboard player, because keyboards had figured heavily into their recordings by way of Billy Payne from Little Feat. He had played on a lot of their records. So they thought this was an opportunity to actually bring a keyboard player out. Jeff threw my name in the hat with the guarantee that I could pull this off. It was not necessary to audition me, just have me show up in a couple of days’ rehearsal and I’ll have it wired. Which, miraculously, I did. I had no money to get to New Orleans, so they paid my way down there. All of a sudden I’m getting a salary that was more than I made in a year with Steely Dan.
I spent the first week with a bunch of little pieces of paper of lyrics and chords taped at the top of my piano. But pretty soon I got to commit all this stuff to memory, and we were off and running. It was just a dream come true. I had this great gig, with another great band. I liked the guys the minute I met them.
For “Taking it to the Streets,” my sister was in college. And not so untypical of college students in the Seventies, she became socially aware and active in a way. There was much discussion about the state of the U.S., where it was going. The college students seem to be aware of the things that most of us who were older and living our lives and working our jobs, we became less aware of. Some of our discussions were about how people seemed to be falling through the cracks, economically. In the inner city, for sure, but even in rural areas. There’s only so many people that were going to benefit from a strictly capitalistic economy. What was going to happen? In the end, what cycle does that set in motion? It seems historically, if you look back, it was always the wars that came from it, and the reform and revolutions that happened. When I wrote the song, I envisioned it being a gospel song. A song I might cut in church with a big choir and a rhythm section. But when the Doobies got a hold of it, it became something different — a rock gospel thing.
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Doobie Brothers, ‘You Belong to Me’ (1977)
That was a real stroke of luck for me. I owe great thanks to Ted Templeman for that one. When I played him the song, I had no lyrics or anything. I had the chords and the melody, vaguely. The Doobie Brothers’ rhythm section had just played on an album of Carly Simon’s [1976’s Another Passenger], and she had cut a version of “It Keeps You Runnin.’” So we got to be friends, and Carly had come down to see us play. She at the time introduced me to David Sanborn, who was a St. Louis compatriot of mine, but I had never met him. We were a generation apart. He was more of a jazz/blues musician, and I was a pop/Top 40 musician in the St. Louis area.
Ted immediately said to me, “You need to get Carly to write the lyrics on this.” I said, “God. If only.” He goes, “I’ll send it to her. Just give me that cassette and we’ll see what she comes up with.” She came up with a lyric immediately and sent back this beautiful handwritten lyric, which I wish I still had today. And we went in and cut the song and I pretty much sang it the way she wrote it. It became one of the songs that, for me as a writer, had a lot of legs. It got covered a lot. More so than other songs of mine. And I really credit Carly’s lyric with that. It seemed to have a universality that got it covered by other artists, especially some female artists. A lot of my songs didn’t really get covered. Not a lot of people did “Takin’ It to the Streets.”
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Doobie Brothers, ‘What a Fool Believes’ (1978)
It’ll always be the most fun for me to play that song with the Doobie Brothers. There’s just something about doing it with the band and their approach to those songs that, for me, will always ultimately be the best version. “What a Fool Believes” was the first tune I wrote with Kenny Loggins, which opened the door to a couple of years of wonderful experiences of writing with Kenny. That raised the whole bar to my songwriting.
It cemented a version of the Doobies that I think might not have happened had that song not made its way into our recording of Minute by Minute. That song was the first thing that put us on the charts. Minute by Minute, as an album, it was like we were TKO’d on the mat and the powers that be at Warner Brothers… We listened to that record at an A&R meeting, and it was a unanimous thumbs down. All the comments were like, “These guys are over. This is a waste of time.”
And when it came out, for some reason, the public just seemed to embrace [it]. Especially “What a Fool Believes.” It took on a whole other life that none of us were prepared for. It just goes to show you how random things can be with records. I don’t even think the radio stations thought it was necessarily a great record or a big hit or even liked the album, but the public did. Somehow the public started requesting the song, and the rest was history.
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Doobie Brothers, ‘Here To Love You’ (1978)
Minute by Minute, we were starting to experiment with our inner gospel child, as a band. We started to explore a little more of a jazz/gospel sensibility. I don’t even know that we knew why we were doing that, but it just seemed like that was the most natural next step for us. A lot of people either credit or accuse me of being the ringleader in that respect, but it was really a group effort. Jeff Baxter and Tiran Porter certainly had as much to do with it as I did. Pat [Simmons] came in with some songs that were more jazz, Barney Kessel chord progressions. The band was always very adventurous in the studio, but all of a sudden we just took this whole other tack with songs that were actually written on keyboards, as opposed to written on guitar and keyboards added. So it took us in another direction.
“Here to Love You” was one of the more gospel things on the record. Once in a while I would stick my head in West Angeles Church in L.A. or someplace, just to hear that music in its natural setting. Because to me, gospel music would reach a level of passion and expression that rock music never did. In its finest hour, there was nothing more exciting to me than gospel music. Especially in that natural setting in church. It reached a level of emotion that I never heard in rock & roll. So that’s why we were pushing in that direction as a band. We were a poor man’s version of it, but we saw that as an avenue.
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Michael McDonald, ‘I Can Let Go Now’ (1982)
I’m famous for writing a song for five, six, maybe 10 years. I’m famous for letting things sit forever until they write themselves. I always had a belief that the song will write itself better than I will, if I just leave it alone and let it happen. But then there’s songs that just pop out. They just fall out of the sky, and “I Can Let Go Now” was one of those. I wondered when it was done, “Did I write this, or did some dead relative send it to me from the other side?” I don’t know.
Within 10 minutes of sitting at the piano, the song evolved. It came from a personal experience. I always wrote in the third person back then. I didn’t really write about my own feelings as much as feelings I observed other people expressing. I had been in a relationship and it didn’t end well. Not that it ended terribly or anything, but it had run its course. When I ran into this person six or seven months later, I was pleasantly surprised to realize that she had forgiven me and that she was genuinely friendly and happy and even asked how I was doing in my new relationship.
I made some attempt to apologize again for the way things had gone down with us. She made the comment, “Oh, that’s OK. Don’t worry about it. It was tough for a while for me and I didn’t understand, but I got to a point where I can let go now.” The minute she said that, I thought, “There’s a song in there.” That’s how sensitive I am. The first thing I thought of was, “That sounds like a song to me.” So that song just came from that statement, and literally the music just fell out of the sky.
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James Ingram & Michael McDonald, ‘Yah Mo B There’ (1983)
“Yah Mo B There” was one of the best opportunities that ever presented itself in my career, which was a chance to work and write with James Ingram. I always marveled at his voice. At his natural ability, and his duets with Patti [Austin]. I remember watching them from the side of the stage once, and listening to them sing literally brought me to tears.
James was an amazingly talented powerhouse personality and just a wonderful guy. We became good friends in the course of working together. One of the things that went beyond our professional relationships — myself and James and with all the Doobie Brothers — was we were all starting to have kids at that time. Our kids were something that we all had in common. They were all around the same age, and we were all suffering from the same catastrophic experiences of being a parent in the music business and trying to raise little kids. It brought us all closer.
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Michael McDonald, ‘Take It to Heart’ (1990)
That’s the one and only song I ever got to write with Diane Warren. I think I had produced a lot of that album [Take it to Heart] myself. It was my first effort to just go in and cut some songs myself. But then at a certain point, we all unanimously agreed that I needed something more. And Don Was came on the scene. Another great stroke of luck. He was going to produce a couple tracks with me — arguably the best tracks on the record. But he suggested I write a song with Diane Warren.
So Diane and I got together at my house in Santa Barbara, and we dove right in and started to write. I learned so much about her and what a real pro songwriter is. While we were writing, every once in a while she’d take a break to go make some phone call to the editors of Billboard to talk about the chart positions of her songs. Things I never would’ve dreamed of doing. I never read a Billboard. Doobies, we’d put out a record and I would just wait for somebody to tell me what was going on.
She was the same way about writing a song. It was a no-bullshit approach. She just knows how to really deliver the knockout punch in the structure of the song. It was like, “This is what this song has to do to be that quintessential hit song on the radio.” There was no room for my usual meandering. And she was right, because that song probably got on the radio faster than any song I ever put out. It just seemed to have that attraction for Top 40 adult contemporary radio that almost no track I had done before ever had. It was harder and harder to get on the radio, but she just seemed to know what it took. I was always forever grateful for that experience. I’ve spent all the time since then wishing I had the chance to write with her again.
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Michael McDonald, ‘You Show Me’ (1990)
I wrote that song with a friend of mine, Harry Garfield. Harry and I go way, way back. We used to play the clubs of L.A. together in bands. But years later, Harry had gone into being an executive at Universal Studios and Universal Records. He was a music director for films. He called me and said, “This film’s being made, and there’s a slot there for a possible song, and I mentioned that you might be able to write it.” And I said, “Well, why don’t we write it together?” So we proceeded to write “You Show Me.”
It was a song that stood on its own, because it had a slow bossa nova feel, which was something I always wanted to write. One of those songs like “The Look of Love” or “Girl From Ipanema.” I love that music and that genre. When we recorded it, Abraham Laboriel, the bass player, was from Mexico and knew how to play that style of guitar. He had a little classical gut-string guitar at home. He drove home and got his guitar, came back, and proceeded to learn the song on guitar for me. And that’s how we recorded the track. I’d love to go in and remix that track, because I felt like we tried to make it a pop-sounding track or a radio-friendly track when really, it wanted to be more of a sparsely arranged, beautiful Brazilian recording. So anyway, that’s the history of that song. I don’t think it made the film.
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Michael McDonald, ‘Blink of an Eye’ (1993)
I remember talking to a receptionist at the studio where Donald Fagen was doing his solo record, or maybe mixing some of the original [New York] Rock and Soul Revue tracks. I was talking to the receptionist as I was leaving, and she goes, “My mother always says be careful when you’re walking down there to get in a cab. Remember to look both ways when you cross the street here in New York.” And I laughed and she chuckled and that phrase stuck with me. Look both ways. I wanted to write something in a New Orleans second line feel. And that phrase kept haunting me.
“Blink of an eye” somehow came into play too, how life is basically the blink of an eye. You’re in high school and the next thing you know you find yourself in your forties. And at that point in your life and where I was at the time — I had kids and I was midlife — you tend to have this other perspective that you couldn’t have at any other time in your life, where you’re looking in both directions. You’re looking behind you to see how you got where you are, and you’re looking ahead to see what all this means and where you might be going. It’s a unique, weird perspective that you may never have again in your life. As you get older, you might tend to look more and more behind you and less and less in front of you.
So that’s what the song became about for me, and it recreated a flood of memories for me of growing up. Television was a big part of our lives growing up in the Fifties. It was this new age of watching political events happen before your eyes. Watching Martin Luther King talk about things that made my parents reassess the reality of the American experience. The history of our country has been largely based on people who come along and make us see things and make us think about it. Our life experience is largely based on what we learned from people like that.
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Michael McDonald, ‘Where Would I Be Now’ (2000)
Joe Cocker did a version of it, which was a thrill for both me and [co-writer] Tony Joe White. One of my fondest experiences is writing songs with Tony Joe White. Tony was a natural. He was that guy that you’d sit down with and just start talking conversationally, and a song was going to come out of that. He saw those opportunities in a much keener way than most of us do. He could twist a line of casual conversation into something and weave it into a song in a heartbeat. I always loved that about him. I knew we were going to come away with a song every time we got together.
That song, for me, was really very autobiographical. I’d been there numerous times by that point in my life. “What is this pattern where, if you invest in me, if you bet on me in a relationship sense, I’m going to disappoint you time and time again, and I’m going to try to salvage it as long as I can till you finally get sick and tired of my bullshit?” That was a part of myself I didn’t really understand. Patterns become bad habits. Especially people who deal with certain issues like addiction, you tend to be self-obsessed, and that always leads you down that path in a relationship that is unsustainable. And that’s what that song was about. Just hanging on by a thread to the last person on the block who’s there for you in a way that other people may not be.
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Michael McDonald, ‘Peace’ (2001)
We were tasked with doing this Christmas album [In the Spirit]. I enlisted the help of [producer] Mark Harris because I knew Mark’s background in gospel music, and I wanted to make a gospel Christmas album. I wanted to have the sincerity of gospel music as a bedrock for this record. I didn’t want to do all the familiar Christmas songs that people typically did. I wanted it to be original songs, for the most part. And that was met with a lot of resistance from the record labels. They wanted me to go in and do a traditional Christmas album. I said, “No. I want to write some of the material.”
They went for that, and we started to cut the record. “Peace” was one of those songs that was just an idea in my head, a storyline from the perspective of the wise men on their search. They’re out there in the middle of the night following a star on a hunch, looking for something that they’re not even really sure of. They’re not even totally cognizant of what it is they’re looking for. They just know that they’re supposed to be on this sojourn and the search for something that’s going to be the answer that they seek to life on a higher level, a higher spiritual plane. Aren’t we all on that search? At some point in our lives, don’t we realize that that’s really what we’re here for — to reach some understanding of ourselves beyond our self-absorbed notions of who we are and our perception of what reality is?
So I immediately called Beth Nielsen Chapman because I love her lyrics, and I knew if anybody could help me flesh this out into an actual lyric and song, it would be her. We sat at the piano and the melody evolved the more she sang it. It started to make the song go places that neither one of us really thought about when we sat down. That’s the way songwriting should go.
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Michael McDonald, ‘Enemy Within’ (2008)
We were doing this record Soul Speak, and we could have done another 10 strictly Motown retrospectives, because there’s that many great Motown songs that charted from the early Sixties through the Nineties. But we decided to veer off and bring in some other songs that weren’t necessarily from the Jobete [publishing] catalog or the Motown label that seemed relevant to that period of time. We widened the playing field a little bit. But we also decided, “Let’s put a couple originals on this album.”
I wrote “Enemy Within” with Simon Climie, my producer on the record. At this point in my life, I was starting to try to write songs about what my own feelings were. Throughout most of my career, I was comfortable writing about somebody else. But if you asked me “How do you feel?” that was a pretty sure way to irritate me, because I wasn’t a person that was comfortable expressing my deepest feelings about anything. I avoided that most of the time. I just grew up being that way. I think it was my attraction to sad songs, too. I never could process sadness or loss in the first person. But I sure loved to hear somebody else on the jukebox in some bar sing about it, and those songs could bring me to tears.
My greatest problems didn’t have anything to do with other people, places, or things that I always historically loved to blame my problems on. My problems really began and ended with me. It wasn’t what happened to me by way of other people or places or events — it was what I did when those things did happen. It was how I reacted. I was the problem. And that was a real light turning on for me. It happened in sobriety. The best two words I ever heard in my life from someone who really wanted to help me in a moment of being newly sober was when somebody looked at me as I complained about all those people who had wronged me and all those things that had happened to me, and they said, “Tough shit.”
And I remember thinking, “That’s exactly right. Tough shit. Who cares? Everybody lives through this stuff. I weaponize it. I make it into something that allows me to keep behaving badly and drinking too much, and it’s always my excuse for the next escape.” That song, for me, was about that place where that begins. That moment where I have to make the choice: Am I going to go where I always go, or am I going to stop and think about this and recognize the enemy within?
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Michael McDonald, ‘Just Strong Enough’ (2017)
“Strong Enough” was kind of in keeping with that. A song that I wrote with Gary Nicholson, who’s a great songwriter. It was an attractive idea to write a blues song, because that was Gary’s background, Americana, blues. I knew he was the guy to help me write a good blues ballad, and I always loved Al Kooper’s “I Love You More Than You’ll Ever Know” [released by Blood, Sweat & Tears] and Willie Dixon’s “Sitting on Top of the World.” Those are songs that I’ve always felt like were classic, slow blues. And so “Strong Enough” was an attempt in that direction for us, and I think we landed on our feet, if I do say so myself. Thanks to Gary, largely.
It’s a song about these impossible situations. A lot of what could be said about the addict alcoholic is, he’s that person that there’s three doors, and he’s just sure that that center door is the right door. Against all logic. He keeps opening it, and there’s a guy on the other side of it with a ball-peen hammer that proceeds to immediately hit him in the forehead with it. And he staggers backwards and the door closes and he says, “Oh Jesus! That hurt.” But rather than pick one of the other doors, he just knows if he keeps trying that same door over and over again, one of these times that son of a bitch with the ball-peen hammer is not going to be there and I’ll be able to walk right through.
And he lives his life that way. “If I just keep doing this, it’s going to work one of these times.” So that’s what that song was about. That relationship where you’re just hanging on for dear life. It’s probably not going to get any better. You’re not going to change the other person. You’re not going to really change your situation until you surrender to the fact that maybe this just isn’t working. But you’re going to hang on to the bitter end and everything that comes along with that.