Easy for me since I shuffle all day at work. I have ~175 albums here at work, so roughly around 1,750 songs or so.

Kings of Leon – Back Down South
The Gaslight Anthem – The Queen of Lower Chelsea
Linkin Park – Robot Boy
Enter Shikari – The Jester
The Go! Team – Buy Nothing Day
Weezer – Run Away
Jónsi – Sinking Friendships
Titus Andronicus – ...And Ever
The Streets – Without Thinking
Cee Lo Green – The Lady Killer Theme (Outro)

Haven't done one of these in a while. I will shuffle while I'm listening sometimes, but my genres are all over the map so I usually just end up playing a Hip Hop only or Rock only playlist depending on what I feel like listening to otherwise I end up skipping through a lot of tracks.

King of Leon - On Call
Jay-Z - Run This Town
Band of Horses - For Annabelle
Weezer - Dreamin'
OutKast - Liberation
Wu-Tang Clan - Severe Punishment
Green Day - Sassafras Roots
The Kooks - Down To The Market
311 - Down
The Sounds - 24 Hours

Subsonic*
749 albums
11,750 songs
73.14 GB (~ 1,136 hours)

01.) Redd Foxx - Live And Funny: Volume 2, Part One
02.) John Lennon - I'm Losing You (Stripped Down)
03.) Death Cab For Cutie - Song For Kelly Huckaby
04.) Nappy Roots - One Forty
05.) the pillows - Hybrid Rainbow
06.) Webstar feat. Young Deion, Rex & Brittany Taylor - Take You Down
07.) Jessica Lea Mayfield - Run Myself Into The Ground
08.) Garbage - So Like A Rose
09.) Kid Cudi - Ashin' Kusher
10.) M.I.A. - Teqkilla
11.) Richard Marx - Rhythm Of Life
12.) Proof & Dogmatic - Everyday
13.) Katy Perry - One Of The Boys
14.) Garfunkel And Oates - Pregnant Women Are Smug
15.) 2Pac - Fuck Friendz
16.) 40 Cal. - Freestyle
17.) La Roux - Reflections Are Protection
18.) Clipse - Keys Open Doors
19.) Pete Droge - Electric Green
20.) N*E*R*D - Happy

*Clicked the first album that came up randomly and selected play random song.

How to Destroy Angels – BBB
Adele – One and Only
Weezer – Memories
Tame Impala – Jeremy’s Storm
The Black Keys – Black Mud
MillionYoung – Gravity Feels
CunninLynguists – Hellfire
Atmosphere – Musical Chairs
Lykke Li – Unrequited Love
Social Distortion – Diamond in the Rough

Home PC:

1. Lamb of God: 11th Hour
2. Book of Black Earth: God of War
3. Lemuria: Yesterday's Lunch
4. Comeback Kid: Industry Standards
5. Unbroken: Zero Hour
6. Agalloch: Hallways of Enchanted Ebony
7. Virgin Black: Midnight's Hymn
8. Ana Moura: Fado das Horas Incertas
9. Finntroll: Vatteanda
10. Javier Navarrete: A Tale (Un Cuento)

iPod 160GB

1. Tricky: Children's Story
2. The Misfits: The Hunter
3. She & Him: Ridin' In My Car
4. Shattered Realm: All Will Suffer
5. Peter Gabriel: Exposure
6. Esham: My Homie Got Shot
7. Reggie & The Full Effect: Lorimer St.
8. Skeletonwitch: Soul Thrashing Black Sorcery
9. Portal: Vessel of Balon
10. Killswitch Engage: Numbered Days

Zune HD 16GB

1. Ke$ha: Grow A Pear
2. Kate Nash: Dickhead
3. A Loss For Words: The Promises You keep (Burn This Bridge)
4. Mastodon: The Last Baron
5. Bayside: How To Fix Everything
6. Lights: Saviour (Acoustic)
7. Portishead: Half Day Closing
8. Madball: Never Had It
9. Gallows: Six Years
10. Rilo Kiley: Ripchord

iPad 64gb (3854 songs)

1. "Where Did You Sleep Last Night?" - Nirvana
2. "Third Eye" - Tool
3. "That Was Just Your Life" - Metallica
4. "Skippin' Town" - The Drums
5. "Come Back" - Depeche Mode
6. "Love is Like a Bottle of Gin" - The Magnetic Fields
7. "Shouldn't Have Down That" - Depecehe Mode
8. "Cool to Hate" - The Offspring
9. "Blame it on the Tetons" - Modest Mouse
10. "To Sheila" - The Smashing Pumpkins

10 more:

"I've Got My Love To Keep Me Warm" - Billie Holiday
"Rich Woman" - Robert Plant & Alison Krauss
"My Funny Valentine (Live)" - Chet Baker
"My Eyes Have Seen You" - The Doors
"Quick and to the Pointless" - Queens of the Stone Age
"Sexy Sadie" - The Beatles
"The Big Payback" - EPMD
"Girl from the North Country" - The Waterboys
"La Descarga Del Bobo" - Willie Bobo
"Baubles, Bangles and Beads" - Wes Montgomery

Ipod classic, 25766 songs

1. PJ Harvey - The Glorious Land
2. Nine Inch Nails - Necropolis (from the Quake soundtrack)
3. The Stone Roses - All Across The Sands
4. Joan Jett - Bad Reputation
5. Brian Eno - Thursday Afternoon (61 minute version)
6. Foo Fighters - See You
7. Patti Smith - About a Boy
8. Melissa Auf der Maur - Head Unbound
9. Cocteau Twins - Flock of Soul
10. Vanessa Mae - Beethoven: Romance #2 in F Major, Op. 50
11. Jimmy Preston - Hucklebuck Daddy
12. Miles Davis - Ghetto Walk (I wish I could find a video of this one. It's over 25 minutes of beauty from the Complete In A Silent Way Sessions)
13. Deerhoof - Siriustar
14. The Detroit Cobras - Try Love
15. Jonsi & Alex (Riceboy Sleeps) - All The Big Trees

HOME PC

Saves The Day- Jukebox Breakdown
Buried Alive- Poisoned Seeds
Tsunami Bomb- Dawn On A Funeral Day
Neurosis- Left To Wander
The Wonder Years- Melrose Diner
Integrity- Burn It Down
Gather- Escalate
Unruh- Complex
Skarhead- Dogs Of War
Minus The Bear- Let's Play In A Five Guitar Band

Zune HD (16GB)

Set Your Goals- Not As Bad
Head Automatica- Scandalous
Buried Alive- Kiss Of Death
The Ataris- The Last Song I Will Ever Write About A Girl
Punch- Mending Is Better Than Ending
Heartsounds- Slave To A Heart That Strays
Misery Index- The Lies That Bind
Ceremony- Nail
Run With The Hunted- Double Zero
Gorgoroth- Prosperity and Beauty

160 GB ipod classic, 25745 songs

1. Kat Emerson - One Fine Day
2. Childish Gambino - Glory
3. Sleater-Kinney - One Beat
4. Lily Allen - Back to the Start
5. Autechre - Dael
6. Madonna - Everybody
7. Blake Babies - Kiss and Make Up (can't find on youtube, watch Out There in its place)
8. Norah Jones - It's Gonna Be
9. They Might Be Giants - Solid Liquid Gas
10. The White Stripes - When I Hear My Name
11. Carina Round - Shoot
12. The Muffs - Is It All Okay?
13. Thea Gilmore - Old Soul
14. William Shatner - Together
15. Kimya Dawson and Antsy Pants - Tree Hugger

Itunes 133 albums

1. Do I know You-Mushroomhead
2. Cast Down-Slayer
3. All of the Lights-Kanye West
4. Weekend Wars-MGMT
5. Systematic Elimination-Cannibal Corpse
6. A Cinderella Story-Mudvayne
7. Force of Nature-Pearl Jam
8. Dragula-Rob Zombie
9. Droppin Plates-Disturbed
10.Eeyore-Slipknot
11.Exile-Slayer
12.The End of the Line-Offspring
13.Hallowed Point-Slayer
14.Our Own Way-Mushroomhead
15.Treehouse-Nada Surf

iPad, 3982 songs:

1. "Underworld USA" - Cold Cave
2. "It Hurts Me All the Time" - Faunts
3. "You're Going to Lose That Girl" - The Beatles
4. "Jynwythek Ylow" - Aphex Twin
5. "Platinum" - Orgy
6. "Alabaster" - Foals
7. "Art Star" - Yeah Yeah Yeahs
8 "Come as You Are" - Nirvana
9. "Bring Your Daughter to Work Day" - Aperture Science Psychoacoustics Laboratory
10. "Fool For You" - Cee Lo Green

iMac -18654 Songs/106.19 GB

1. WC - Rich Rollin'
2. MXPX - GSF
3. Usher - Radar
4. Paramore - Whoa
5. Esso - Just Feel It
6. Notorious BIG - Machine Gun Funk
7. WC - Ain't A Damn Thing Changed
8. Ryshon Jones - Evil With In
9. Calvin Harris - This Is The Industry
10. 2Pac - It Ain't Easy

1. The Naked and Famous - Young Blood
2. Crosby, Stills, & Nash - Judy Blue Eyes
3. The Knife - Heartbeats
4. Skrillex - Scary Monsters and Nice Sprites
5. Prince - The Beautiful Ones
6. Pink Floyd - Have a Cigar
7. Electric Light Orchestera - Evil Woman
8. David Bowie - Heroes
9. Yes - Changes
10. Motley Crue - Black Widow

Let's see what comes up today.

Ipod Classic 160 GB: 25787 songs

Every link leads to a youtube video of that song.

1. Descendents - Everything Sux
2. Mogwai - Yes! I Am A Long Way From Home
3. Yeah Yeah Yeahs - Sheena Is a Punk Rocker
4. Camera Obscura - Books Written For Girls
5. They Might Be Giants - Asbury Park (Stone Pony)
6. Laura Cantrell - 14th Street
7. Underworld - Juanita / Kiteless / To Dream Of Love
8. Tori Amos - Enjoy The Silence
9. Dirty Projectors - The Bride
10. Patty Griffin - When It Don't Come Easy
11. Laurindo Almeida & The Danzaneros - Big Town
12. Miles Davis - But Not For Me (Take 1)
13. Mieka Pauley - Draped in Blue
14. Miss Tammy Faye Starlite - Did I Shave... (NSFW)
15. Tilly and the Wall - Black and Blue
16. Beck - Que Onda Guero
17. Collective Soul - The Bugaloos
18. Aphex Twin - Gwarek2
19. Sarah Fimm - Counting Waves
20. Helios - A Mountain of Ice

Ok, I think I'll stop now.

Zune HD 16GB

Sade- Somebody Already Broke My Heart
Disembodied- Devil's Grin
Candiria- Signs of Discontent
Massive Attack- Better Things
Murder By Death- Ball & Chain
Emperor- The Acclamation Of Bonds
Rilo Kiley- Glendora
Punch- Rewrite
13 Steps- The Survivor
Oathbreaker- Hierophant
Katy Perry- One Of The Boys
Superbus- A La Verticale
Ghoul- Rot Gut
Howl- And The Gnawing...
Seven Generations- In Wolves Clothing

Re-sync'd my Nano (which I haven't did in ages) let's see what we get:

Attack - System of a Down
I'm Serious - T.I.
La La La He He - Prince
Dog Eat Dog - AC/DC
Painkiller - Judas Priest
Trash - Korn
Pinhead - Ramones
Jesus, Mary and the Holy Ghost - Dio
Blitzkrieg - Metallica
State Of Mind - Clint Black

Itunes- 13,296 songs 67.34GB.

Flower Kings- Touch My Heaven
Guns N Roses- Mama Kin
Breeders- When I was a Painter
Liquid Tension Experiment- Another Dimension
Alice in Chains- A Looking in View
Symphony X- Pharaoh
Winger- Without the Night
Andrew Dice Clay- Double Parking
Liz Phair- Shitloads of Money
PJ Harvey- Electric Light

Zune 120 GB. 14,475 Songs.

Cannibal Corpse - Bloody Chunks
Soilwork - Light Discovering Darkness
Enslaved - Queen of Night
Enslaved - Singular
Terrorizer - Strategic Warheads
Hypocrisy - Killing Art
The Professionals - Has Anybody Got an Alibi
Iron Maiden - Still Life
Anna Aaron - The Drainout
Veneficium - Marcia Funebre
Bruno Nicolai - Murder in the Elevator - From the film Perché quelle strane gocce di sangue sul corpo di Jennifer aka What are those Strange Drops of Blood Doing on Jennifer's Body aka Curse of the Bloody Iris
Judas Priest - You Say Yes
The Birthday Massacre - Pale
The Alan Parsons Project - Voyager
Delerium - Remembrance
Flock of Seagulls - Nightmares
Turbonegro - Selfdestructo Bust
The McCain Brothers - Guandi Theme (from My Name is Bruce)
Scarling - Bummer
Kregg Nance - You're Eating Out My Heart and Soul (from Motel Hell)
Wolves in the Throne Room - Woodland Cathedral
Daft Punk - The Grid (Tron Legacy)
Suidakra - The Ember Deid (Part II)
Amethystium - Shadowlands
Iron Giant - I Need To

James Brown - "Try Me (Live at The Apollo)"
Nick Drake - "I Was Made to Love Magic"
J.J. Cale - "Where the Sun Don't Shine"
Chet Baker - "They All Laughed"
Fatback Band - "Goin' To See My Baby"
Bootsy Collins - "Bodyslam"
Leonard Cohen - "Last Year's Man"
Ladytron - "Skool's Out..."
Sugarhill Gang - "8th Wonder"
Horace Silver - "Finger Poppin'"

1 Afrika Bambaataa & Soulsonic Force - Planet Rock
2 The Dream Academy - Life in a Northern Town
3 Joe - I'm in Luv
4 Gary Numan - Cars
5 Tisha Campbell - Push
6 Re-Flex - The Politics of Dancing
7 Guy - Wanna Get With U
8 Lo-Key? - The Shawanda Story
9 Everlast - I Got the Knack
10 Another Bad Creation - Iesha

.

Zune 80g: 12755 Songs

1. Xanadu - Olivia Newton John
2. Closer - NIN
3. Reading in Bed - Emily Haines
4. The Rose with the Broken Neck(featuring Jack White) - Danger Mouse & Daniele Luppi
5. Shameless - Ani DiFranco
6. Zoo Station - U2
7. Daughter (2011 Remaster) - Pearl Jam
8. Marco Polo - Loreena McKennitt
9. Stay - Lisa Loeb & Nine Stories
10. Won't Want for Love (Margaret in the Taiga) - The Decemberists

Alright, based on recent criticisms, I've decided to do a new one...coooome on, diversity!!

Kiss - god Gave Rock n Roll To You
Ignite - Slowdown
Small Brown Bike - Just Bones
Faith No More - Epic
Sick Of It All - Let Go
Strung Out - Velvet Alley (acoustic)
David Lee Roth - Tobacco Road
Title Fight - Safe in Your Skin
Glassjaw - Miracles in Inches
Hot Water Music - Russian Roulette

nice!

It's been a while...

32GB iPhone 4/1520 songs

Ulver - Hiertets Vee
Agalloch - The Isle Of Summer
Wolves in the Throne Room - I Will Lay Down My Bones Among the Rocks and Roots
Ghost - Satan Prayer
Toxic Holocaust - The Liars Are Burning
Butthole Surfers - Ghandi
Samhain - In My Grip
Of The Wand and the Moon - Summer Solstice
Graveyard - Ungrateful Are the Dead
Nine Inch Nails - Sanctified

Foo Fighters - All My Life
Alice in Chains - I Can't Remember
the Offspring - Genocide
Wolfmother - White Unicorn
The Beach Boys - Let the Wind Blow
Paul Gilmartin - A Christmas Poem
John Williams - The Imperial March
Karelia - Slave of Time
Temple of the Dog - All Night Thing
Chicago - Along Comes a Woman

iTunes: 12,382