Loudon Wainwright III

Loudon Wainwright III
Hugh’s Room, Toronto
April 13-14, 2011
by Lisa McDonald
Live Music Head

The son of a yoga teacher and a Life Magazine writer, Loudon Wainwright the Third was born an American on September 5, 1946 in Chapel Hill, North Carolina. The eldest of his parent’s four offspring, Wainwright grew up in Westchester County, New York and Beverly Hills, California, with a third grade crush on Liza Minnelli, who happened to be a fellow classmate.

In 1956, Loudon bought his first record, All Shook Up by Elvis Presley.  It was another five years before Bob Dylan became his musical role model, after seeing him perform at the Newport Folk Festival.  In the early 60s, the budding guitar player was sent off to St. Andrew School for Boys (seen in the film Dead Poets Society), the same school Loudon Wainwright the Second went, twenty years earlier.  Loudon and his father also shared the same shrink at one time. Upon graduating from St Andrew in 1965, Loudon went on to drama school at Carnegie Mellon in Pittsburgh, but dropped out in ‘67 when he decided to head to San Francisco for a Summer of Love.  Years later, Wainwright’s School Days appeared on his first album.  And in Toronto this week, he performed it as an encore on the second of a two-night run at Hugh’s Room on Dundas St W...

“In Delaware when I was younger
They thought St. Andrew had sufficed
But in the spring I had great hunger
I was Buddha. I was Christ
You wicked wise men, where’s your wonder?
You Pharisees one day will pay
See my lightning, hear my thunder
I am truth. I know the way”

Busted for pot in Oklahoma around the age of twenty, Wainwright got a free haircut during his five day stint in the slammer, before his dad arrived to bail him out. To pay the Second back, Loudon worked as a movie house janitor, boatyard barnacle scraper, and as a cashier-cook-dishwasher at New York City's first macrobiotic restaurant,  the Paradox on East 7th St.  This was around the time he began writing his own songs.

The first song Loudon Wainwright ever penned was called Edgar, about a Rhode Island lobsterman.  Singer-songwriters were very popular in 1969, and after hooking up with Milton Kramer who became his manager, LWIII signed a deal with Atlantic Records.  But with more than 25 albums released since then, on something like eight different labels, apparently only one of his songs was deemed chart-worthy. 1972’s Dead Skunk in the Middle of the Road reached number one for six weeks in Little Rock, Arkansas.

In 1975, Wainwright pursued an acting career and made his debut playing Capt Calvin Spaulding, the singing surgeon, in three episodes of M*A*S*H, the critically-acclaimed dramedy whose series finale  became the most watched episode in U.S. television history. Coincidentally, one of those same three episodes aired at 5pm on the History Channel on Wednesday,  the first day of Loudon’s two-night run at Hugh’s Room.  In a 5th season episode of Saturday Night Live, Loudon was the musical guest and performed two songs.  He was also David Letterman’s original sidekick before daytime turned to nighttime and Paul Shaffer came along.  He’s made several appearances in motion pictures such as Big Fish, The Aviator, Elizabethtown, and the 40-Year-Old Virgin, and also had a recurring role in Undeclared, Judd Apatow’s short-lived 2001-02 television sitcom centered on a group of college freshmen, particularly the geeky Steven.  Loudon played Steven’s father, who in the throes of a mid-life crisis, shows up on campus to hang out with his son’s friends, to the great embarrassment of Steven.

From Harry’s Wall on 1988’s Therapy: "I guess by now you’ve noticed / Almost all the songs I write / Somehow pertain to me" is only one of many song lyrics that show this talented artist as the confessional songwriter and singer of autobiographical songs that he is. Clever and cunning, smart and satirical, the poetry of his work can be downright hilarious, but at the same time heartwrenchingly sad. And the darkness, anger, and bitterness can put some listeners off.  Wainwright moved to London in 1985 after discovering he received more notice in England than in the U.S.  He did however receive a Grammy nomination the same year, for the album I’m Alright. After the staff of Hugh’s delivered a glass of red wine to the stage last Wednesday, Wainwright played the title track from said album. A song about being on the road and down and out, following a failed relationship. It finishes off with a funny and positive twist, however after performing it, Loudon said, “But we’re not alright, that’s why we’re here”.  He’s got that right.  Another nod from the awards people came in 1986 for the album More Love Songs.  Both Grammy nominated records were co-produced by British singer-guitarist Richard Thompson, but Loudon lost the award on both counts to his good friend, the late Steve Goodman, singer-songwriter of City of New Orleans, a song made popular by Arlo Guthrie. The third tune on More Love Songs will stop you in your tracks. And you could hear a pin drop in Hugh’s Room the moment Loudon sang the opening line...

“Your Mother and I are living apart
I know that seems stupid, but we weren't very smart
You'll stay with her, I'll visit you
At Christmas, on weekends, the summertime too
Your Mother and I are not getting along
Somehow somewhere something went wrong
Everything changes, time takes its toll
Your folks fell in love, loves a very deep hole
Your Mother and I will do all we can do
To work this thing out and to take care of you
Families get broken, I know it's a shame
It's nobody's fault, but you're not to blame
Your Mother and I are both feeling bad
Things will get better, it won't stay this sad
And I hope when you grow up, one day you'll see
Your parents are people, that's all we can be”

Mr Wainwright finally did win a Grammy.  But before he did, he wrote a song about what it might feel like to win, and sang it at Hugh’s on Thursday night...

“Last night I dreamed I won a Grammy
It was presented to me by Debbie Harry
Right up there on stage in my tux
I gulped and said aw shucks
I’d like to thank my producer and Jesus Christ
The audience gave me a standing ovation
I shed tears of joy
I shed tears of elation
Behind the podium there
Debbie grabbed my derriere
I’d like to thank my producer,
and Jesus Christ”

Wainwright has been dubbed “the Woody Allen of Folk" and "the Charlie Chaplin of Rock".  He’s also been described as a "not-so-sensitive folk singer".  But Wainwright’s finely tuned wit served to separate him from the pack, building a cult following with his funny, biting, and incisive songs.  He’s also been described as "a thoroughly compelling master of irony", and in Rolling Stone magazine, "our greatest pop satirist." The first real exposure to LWIII for this writer came by way of Career Moves, released in 1993. The live recording includes The Man Who Couldn't Cry, a song Johnny Cash covered in 1994.

On the live recording So Damn Happy, composer-pianist Van Dyke Parks can be heard saying “Loudon Wainwright is one of a kind, and he should be allowed to coast”. The Hugh’s Room shows were full of Wainwright’s brilliant original material, and from this same live recording, he served up one about the afterlife, and what we all have to look forward to...

“There'll be lots of drinking in Heaven
Smoking and eating and sex
What you didn't do in this life bad for you
Will be totally cool in the next
In Heaven there'll be beer for breakfast
At lunch it's sambuca and wine
The gazpacho with dinner is made with paint thinner
And the morning hereafter feels fine”

But according to his own liner notes, Wainwright entered a period of deep depression following the death of his mother in 1997, believing he would never write again. Retreating to a cabin in the woods,  he gradually recovered and in 2001 released the soul-baring Last Man on Earth, a recording placed very high in Live Music Head’s top five.  White Winos, the third track from the album, guaranteed to give anybody pause, was played at Hugh’s on both nights...

“Mother liked her white wine
She'd have a glass or three
We'd sit out on the screen porch
White winos mom and me
We'd talk about her childhood
and recap my career
When we got to my father
that was when I'd switch to beer”

Loudon is the father of Rufus Wainwright, an artist so talented, Elton John labelled him "the greatest songwriter on the planet". Loudon talked about his son at Hugh’s on both nights, and apparently there was a family gathering recently that celebrated the new arrival of Rufus’ first child. The mother of the baby girl is Lorca Cohen, daughter of Leonard. Clearly the Wainwright clan is expanding upon it’s pool of musical genius. Loudon is also the father of Martha Wainwright, who, like her dad, writes about personal uncertainty, insecurities, and emotional fracture;  songs that expose fears about her own talent, her relationships with the opposite sex, and love in general. These two children are from Loudon’s first marriage to the highly regarded Canadian folk singer, the recently deceased Kate McGarrigle. The sister of Anna was mentioned twice over the two nights at the folk club on Dundas West; once in Red Guitar, and in an unfamiliar song that gave an emotional jolt when Loudon sang about the realization he’s outlived both his father, and his ex-wife.

Daughter Lucy Wainwright Roche is also a singer-songwriter who came into the world by way of Loudon’s second wife Suzzy Roche, founding member of the singing sister trio The Roches, staples of NYC’s Greenwich Village of the mid-70s, who continue to make music today. Loudon remarried for the third time in 2005 to Ritamarie Kelly, a film actress.  LWIII is also the brother of Sloan and Teddy Wainwright, who also carry the musical gene.

In the 2005 dvd, BBC4 Sessions, Wainwright talks about songwriting and compares the process of his early days to that of the mid-2000s... “At this point, weeks or even months will go by and I won’t write anything and think, oh my god it’s over. It’s kinda like sex in that way. So I get some Viagra (laughs).... no.  But I will go into a panic because I think of myself as a singer-songwriter, and if I don’t write any songs, then it’s like ‘I’m an out of work actor’, ya know. So then I say, ‘oh I better write a song’. I kick my own butt so to speak, and write a song. That’s how it’s done now. But when I was younger, much younger, I was writing songs all the time. In that way, it’s also like sex. I was exploding with songs!  Five in a day sometimes! (laughs)”.

Collaborating with Joe Henry to compose  the soundtrack for the film Knocked Up starring Seth Rogen and Katherine Heigl, resulted in 14 songs that were released in 2007. Loudon also made an appearance in the movie, as Heigl’s obstetrician.  Live Music Head was really hoping  to hear Strange Weirdos from that record, but hearing Grey in L.A. in the intimacy of Hugh’s Room certainly sufficed.

In early 2010, Wainwright won the Best Traditional Folk Grammy for High Wide and Handsome, a tribute to the legendary, yet obscure, Charlie Poole.  Loudon talked about Poole at Hugh’s; how the singer-banjo player who drank himself to death had a big hit in 1925 with Don’t Let Your Deal Go Down, a song covered in more recent years by the Grateful Dead.  Wainwright performed the title track from his award-winning album, along with Rowena.

Loudon's latest release is the aptly titled 10 Songs For the New Depression, a collection of topical songs in answer to today’s economic climate, released on his own label Cummerbund Records. When Wainwright asked the Toronto audience if times were as tough here as they are in the United States, there were a few “hmmms” and “ummms”. “Perhaps it's just as bad here, but you’re all just more polite?” Folks then yelled out their varying perceptions, but when I piped up and said things here are “very hard”, Wainwright immediately sang...

“Last man in D.C., he had eight years
Now the whole damn country is in arrears
We got two, three, four wars goin' on
All I can do is play this song
Times is hard. Times is rough
I guess you folks need some cheerin' up
Well it ain't me babe
You got that wrong
All I can do is play this song”

House, a song about trying to sell one in today’s struggling market was played on the first night; and is a personal favourite from the new record.

The toe-tappin’ old sing-a-long favourites, Down Drinking in the Bar and the Swimming Song may have been responsible for rousing a clap-a-long crowd at Hugh’s Room, but the second night must be noted for Tonya’s Twirls, a true Wainwright classic about the disgraced 1991 U.S. Figure Skating Champion, Tonya Harding...

“You knew she was in trouble when you saw her bodyguard
When you saw those two together you knew it wasn't hard
To see that she was different, not just one of the girls
With their gliding and their sliding and their pirouettes and twirls
Then it turned out that she smoked and drank and posed practically nude
She didn't smile all of the time, she got angry and was crude
No she wasn't goody two-skates like all the other girls
With their grinning and their spinning and their winning little twirls”

Dead Man, a song about the late Loudon the Second and the closets of his NYC apartment, which Loudon rummaged through before it was sold two years ago, was also played on both nights at Hugh’s; a new song requiring a lot more listens.  But I would have to say the Hugh’s Room song highlite overall came with A Guilty Conscience and a Broken Heart.  A song that combines all three of Wainwright’s favourite subjects:  death, decay and unhappy dysfuntional love.  As soon as Wainwright sang the opening line, a fella from the audience yelped his approval whereupon Loudon came to a full stop. “Now how do you know this song?, Wainwright asked. I haven’t recorded it”. The reply that came from the hushed crowd was,“I saw it on the internet”. Ol’ Loudo’s response was, “Ah, so you owe me more money then! We’ll meet in the back later.” A touch of nervous laughter rippled through the crowd, which is also something Loudon is good at, making you squirm in your seat, never quite so sure.

“Little did you know that when you dumped me
You’d get a guilty conscience and a broken heart
They pulled back the sheet and I i.d.’ed you
Seeing you so blue gave me a start
Then they slid your body back into the deep freeze
Now you got a frozen broken heart
A guilty conscience and a broken heart
You sure got your comeuppance for your crimes
A guilty conscience and a frozen broken heart
That combo platter does it every single time”

With a great wealth of recorded material already out there, hardcore fans are thrilled to learn that a Loudon Wainwright III career-spanning  4 cd/1 dvd box set, including a 40-page booklet, is set to be released by Shout! Factory on May 3, 2011. 40 Odd Years is highly anticipated, but where Mr Wainwright shines best is on the stage, in a live setting. To quote Musician’s Flanagan, “His relationship with his audience is at once antagonistic and naked. Wainwright is a hammy extrovert, making faces as he sings, lifting one leg in the air, sticking out his tongue and then, unexpectedly,opening his veins for the audience’s inspection." Wainwright told Flanagan,“But I would be bullshitting you if I said that I don’t want to be more successful. I’m obsessed with success and failure.  And I’m frustrated because I’m on the periphery of the music business.” I don’t know if those reading this article would concur, but I’m immensely fond of, and thank god for, this particular music business periphery.

Loudon Wainwright III official website...

Hugh’s Room


Lisa McDonaldAbout Lisa McDonald: Otherwise known as Live Music Head, Ms McDonald is a vegetarian who enjoys practicing yoga and pilates, but it’s an enormous passion for music that keeps her tapping away at a keyboard.  A freelance music writer living in downtown Toronto, Lisa is currently in conversation with musicians and entertainers, sharpening interview skills and publishing articles at web-based magazines.  She may be contacted at: This email address is being protected from spambots. You need JavaScript enabled to view it.


Last modified on Thursday, 19 March 2015 18:47

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