Christopher tracked this one down. Not a bad time at all. You start with the questions in bold, then you turn your music player to shuffle and take the songs as they come as your answers. Of course, I did it nine times and then put the answers in some sort of approximate order (funniest/most pertinent/least pervy and moving down from there). Some with notes.

What does next year have in store for me?
Northern Lights - Swollen Members
Hard Times - Run-D.M.C.
Love Alone - Caedmon's Call
Sleeping in My Car - Roxette
Sometimes Always - Jesus and Mary Chain
(Love Is Like A) Heat Wave - Martha & the Vandellas
Anybody Else But Me - Odds
Truman Show - Sweatshop Union
Sweet Caroline - Me First and the Gimme Gimmes

What's my love life like?
Strange Bedfellows - Spirit of the West
I Get Around - The Beach Boys
Hurting on the Outside - Northey Valenzuela
Steaming - Sarah McLachlan
Fresh as That - Farm Fresh
Lights Down Low - Joel Plaskett Emergency
O.P.P. - Naughty by Nature
Video Bargainville - Moxy Früvous
Cartoons (Live) - Chris Rice

What do I say when life gets hard?
Slow Down - Duotang
Peacocky - Andy Creeggan
Gonna Take Some Time - Chad Doran
You're Here - Sixpence None the Richer
Thin Line Between Love and Hate - Annie Lennox
Aside - The Weakerthans
Share the Land - The Guess Who
Die Jugend Marschiert - Propagandhi
Perpetrators of Art - The Paperbacks

What do I think when I get up in the morning?
Try Again - Aaliyah
Bring on the Dancing Horses - Echo & the Bunnymen
Dance With Me - The Dollyrots
He Will Do For You - Patsy Cline
Oh, Alberta - Elliott Brood
Carefree Highway - Gordon Lightfoot
Come On - Tegan and Sara
Tuktoyaktuk Hymn - Veda Hille
Joe Van Gogh - Dan Bern

What song will I dance to at my wedding?
Unter Dem Doppeladler - FSK with David Lowery (face it, my wedding is going to be awesome)
Science Fiction Music - Hi Lo Trons
Wave of Mutilation - The Pixies
You Can Have Him - Nina Simone
I Can't Believe It - Keith Green
Does it Make You Rain - Justin Rutledge
More Precious Than Silver - Nitro Praise
Cherish - The Partridge Family
How Great Are You Lord - Robin Mark

What do I want as a career?
D.J. - David Bowie
Girl in Green - Blue Rodeo (if only it was a job)
Mountain of God - Third Day (how could that not be worthwhile?)
Book Smart, Street Stupid - Sarah Slean
Push Back the Darkness - Rise Up
Let Your Backbone Slide - Maestro Fresh-Wes
Big Galoot - Nathan
If I Had a Rocket Launcher - Bruce Cockburn
Gun St. Girl - Luke Doucet

What is my favourite saying?
Fjarskanistan - Amina (why, I believe I said that three times today)
How to Bag Your Turkey - Greenfield Main
Look Up - Stars
On the J.O.B. - Mood Ruff (definitely need to start using that one)
What the World Needs Now is Love - Jackie DeShannon
Salvation Belongs to Our God - Crystal Lewis
Touch Your Woman - Dolly Parton
Good Luck - Basement Jaxx
Canoe Song at Twilight - Eileen McGann

What is my pet's name?
1st Lady - Sarah Harmer
Cheesecake - Louis Armtrong
Drunken Sailor - Great Big Sea
Life, in a Nutshell - Barenaked Ladies
Harley Davidson - Serge Gainsbourg
The Denominators - Empiricals
Jericho - k.d. lang
Juliette - Jr. Gone Wild
Kathy's Song - Simon and Garfunkel

What is my favourite place?
Wonderland - The Commodores
Will the Circle Be Unbroken - the Nitty Gritty Dirt Band, Del McCoury, Marty Raybon, Marty Stuart and Friends
Jump Around - House of Pain
In It Now - Rheostatics
Following the Leader - Peter Pan
Dime Song - Plad
Flash - Queen
Starman - Seu Jorge
Two Nations - The Streets

How would I describe my sexlife?
Alleged - The Beta Band
Get Up, Stand Up - Bob Marley
Clumsy - Our Lady Peace
De Do Do Do, De Da Da Da - The Police
On the Ill Tip - LL Cool J
Hearts and Bones - Paul Simon
Several Miles - Ron Sexsmith
Tell Him - The Exciters
King Louis - Dino Martinis

What do I think of my parents?
Mothers Talk - Tears for Fears
Al Final Del Camino - Boyz II Men
Make Us One - Cindy Morgan
House of Gold - Andy Stochansky
Lay All Your Love on Me - Abba
It Must Be Love - Madness
Let's Take a Ride - Justin Timberlake
Reasons Why - Nickel Creek
Party - Kris Kross

What's my superhero name?
Verbal Anime - The Herbalizer
Ladyflash - The Go! Team
Lemon - U2
Surely God is With Us - Rich Mullins
La dispute - Yann Tiersen
Soupy Sayles - Jim Bryson
Can't Cry Anymore - Sheryl Crow
Natural Blues - Moby
Ain't Nothing Like the Real Thing - Marvin Gaye and Tammi Terrell

Where would I go on a first date?
Ah, Singapore - Shonen Knife
Nobodycallsmeunlesstheywantsomething - Shout Out Out Out
Football Song - Stompin' Tom Connors
Californication - Red Hot Chilli Peppers
Main and Broadway - Cub
San Juan - Daniel Lanois
Just Over in Heaven - Doyle Lawson and Quicksilver
What I Don't Know (is Hurting Me) - Bob Snider
Juveniles Don't Stop - Max Webster (PERVY!)

What is my drug of choice?
Piggies - The Beatles (mmmm, ham)
This Is the Song of Sweet Sweet Season When Cherry Garcia Blossoms Bloom - Puffy Ami Yumi (read: lots of acid)
Ca Sent Si Bon De France - Maurice Chevalier
Tishomingo Blues - Garrison Keillor
Blackhole Sun - Paul Anka
Brimful of Asha - Cornershop
Cruise Control - The Inbreds
Stoned Blue - Jimmy Rankin
Sally - Gogol Bordello

How would I describe myself?
Smartbomb - Huevos Rancheros
L'Accordéoniste - Edith Piaf
Waiting in Canada - Jann Arden
Rusting in the Rain - The Kingston Trio
Femme Fatale - R.E.M.
We're Not Gonna Take It - Pigeon Hole
Lost and Stolen - Kevin Hearn and Thin Buckle
Sons and Daughters - Craig Northey
War - The Cardigans

What is the thing I like doing most?
Long Time Running - The Tragically Hip
Learn - hHead
Wicked and Weird - Buck 65
Journey to the End of the Night - The Hylozoists
Love Rollercoaster - Ohio Players
Three or Four - The New Pornographers
Soother - The Waltons
Sleepyhouse - Blind Melon
P.Y.T. (Pretty Young Things) - Michael Jackson (EXTRA PERVY!)

What is my state of mind like at the moment?
Bells On - Sloan
He!She!You!Me!They!We!Us!Ok! - You Say Party We Say Die
She's Automatic - Rancid
Me and the Devil Blues - Cowboy Junkies
Take Me Home - Holly Cole
Suitcase Calling - The Polyphonic Spree
All Star - SmashMouth
Disco Duck - Rick Dees and His Cast of Idiots
Mrs. Potter's Lullaby - Counting Crows

How will I die?
Circus Song - The Gandharvas
Floating Away (In a Bathtub) - Toploader
Spanish Bombs - The Clash
Happy Cycling - Boards of Canada
Steven's Last Night in Town - Ben Folds Five
Your Next Bold Move - Ani DiFranco
Arch Support Blues - Jughead (could you conceivably croak as a direct result of bad arches?)
Goodnight, My Someone - Kristin Chenoweth (Oh awesome--alone and sleepy)
Last Train to Clarksville - The Monkees