Loudon Wainwright III has had a charmed life. The singer/songwriter has captivated audiences for decades with his witty, self-deprecating style. He's also done an impressive job of passing on his musical gift through genetics; children Rufus, Martha and Lucy Wainwright Roche are all accomplished singer/songwriters in their own right. But his latest project is all his to celebrate: a box set spanning his idiosyncratic career, coming out in May on Shout! Factory.

40 Odd Years is to be a four-CD/one-DVD box collecting 87 tracks and three hours of live performances on video. The 40-page book of liner notes will include an essay by David Wild of Rolling Stone. Film fans will recognize an interesting name as co-producer of the set: writer/producer/director Judd Apatow. The influential funnyman behind The 40-Year-Old Virgin, Knocked Up and Freaks and Geeks has been a longtime fan of Wainwright, having cast him in his underrated television show Undeclared and tapped the songwriter to compose the score to Knocked Up.

Thus far, the biggest story revolving around 40 Odd Years is a short article from The Los Angeles Times. But rest assured, more information will be posted to The Second Disc as it comes!

UPDATE 2/18: Well there you have it. Shout! Factory's got this one to order (first 200 copies have their booklets signed by Wainwright!), and MusicTAP has the press release and track list (the latter of which is after the jump).

Loudon Wainwright III, 40 Odd Years (Shout! Factory, 2011)

Disc 1: 1969-1983

1. School Days
2. I Don't Care
3. Uptown
4. Be Careful There's a Baby in the House
5. Saw Your Name in the Paper
6. Dead Skunk
7. New Paint
8. Drinking Song
9. Swimming Song
10. Dilated to Meet You
11. Down Drinking At the Bar
12. The Man Who Couldn't Cry
13. Whatever Happened to Us?
14. Crime of Passion
15. Kick in the Head
16. Summer's Almost Over
17. Just Like President Thieu
18. Golfin' Blues
19. The Heckler
20. Natural Disaster
21. Red Guitar (Live)
22. Hollywood Hopeful (Live)
23. IDTTYWLM
24. The Grammy Song

Disc 2: 1984-1995

1. Westchester County
2. I'm Alright
3. Screaming Issue
4. Unhappy Anniversary
5. Your Mother and I
6. Synchronicity
7. Hard Day on the Planet
8. You Don't Want to Know
9. Bill of Goods
10. Thanksgiving
11. Your Father's Car
12. When I'm At Your House
13. The Picture
14. Men
15. So Many Songs
16. Tip That Waitress (Live)
17. I'd Rather Be Lonely (Live)
18. April Fool's Day Morn (Live)
19. The Acid Song (Live)
20. IWIWAL
21. A Year
22. Dreaming

Disc 3: 1996-2010

1. So Damn Happy
2. Primrose Hill
3. Bein' a Dad
4. Four Mirrors
5. It's Love and I Hate It
6. Christmas Morning
7. Pretty Good Day
8. White Winos
9. Bed
10. Surviving Twin
11. The Shit Song (Live)
12. Between (Live)
13. My Biggest Fan
14. When You Leave
15. Make Your Mother Mad
16. Daughter
17. Grey in L.A.
18. Muse Blues (Recover)
19. Motel Blues (Recover)
20. The Deal
21. Rowena
22. High Wide & Handsome

Disc 4: Rare & Unreleased

1. Weave Room Blues (with Kate McGarrigle)
2. McSorley's
3. Black Uncle Remus (Demo with Band)
4. Funny Having Money
5. The Hardy Boys At the Y (with The Boys of the Lough)
6. Laid
7. Outsidey
8. Somethin' Stupid (with Barry Humpries)
9. The Miles
10. So Good So Far (Live from The Bottom Line)
11. Big Fish
12. No Sure Way
13. Hey There Second Grader
14. More I Cannot Wish You
15. Florida (Lucky You)
16. Hank & Fred (live at KGSR, Austin, TX, Dec. 5, 2003)
17. Your Eyes
18. Dead Man
19. At the End of a Long Lonely Day (with Suzzy Roche)

Disc 5: DVD

1. One Man Guy (1993 Dutch television documentary)
2. One Man Guy - BBC4 Session, Bush Hall, London - 5/2/2005

• One Man Guy (BBC4 Session, Bush Hall, London - 5/2/2005)
• Heaven (BBC4 Session, Bush Hall, London - 5/2/2005)
• When You Leave (BBC4 Session, Bush Hall, London - 5/2/2005)
• Half Fist (BBC4 Session, Bush Hall, London - 5/2/2005)

1. Loudon Wainwright III at the BBC (aired 9/23/2005)

• Reciprocity
• Roll in My Sweet Baby's Arms
• Unrequited to the Nth Degree
• Dump the Dog and Feed the Garbage
• Glad to See You've Got Religion
• Motel Blues
• Rufus is a Tit Man
• Cardboard Boxes
• Thanksgiving
• Hitting You
• Career Moves

1. Dead Man (recording session documentary, 5/24/2010)
2. The End Has Begun (with Martha Wainwright) (Live on Entertainment Desk, Canadian television, 1995)
3. My Mother and My Sweetheart (with Rufus Wainwright) (from High Wide & Handsome - The Charlie Poole Project 2009 documentary)
4. Needless to Say (with Lucy Wainwright Roche) (Live on The Basement, Sydney, Australia - 2008)
5. Lullaby (Live on Austin City Limits - 1/13/1988)
6. Living Alone (Live on Austin City Limits - 2/16/1999)
7. Homeless (Live on Austin City Limits - 2/16/1999)
8. Tonya's Twirls (Live on Austin City Limits - 2/16/1999)
9. OGM (Live on Austin City Limits - 2/16/1999)
10. Bicentennial (Live on Saturday Night Live - 11/15/1975)
11. Unrequited to the Nth Degree (Live on Saturday Night Live - 11/15/1975)
12. The Garfield House (May 24, 2010)

• New Paint (with Joe Henry & Greg Leisz)
• Absence Makes the Heart Grow Fonder (with Joe Henry & Greg Leisz)
• Roll in My Sweet Baby's Arms (with Christopher Guest)
• June Apple (with Christopher Guest)
• Unhappy Anniversary (with Christopher Guest)
• Kings and Queens (with George Gerdes)

1. Grey in L.A. (826LA Benefit - 1/16/2007)
2. Daughter (826LA Benefit - 1/16/2007)
3. Kick in the Head (Live on PBS Soundstage - 2/2/1977)
4. Passion Play (Live at McCabe's Guitar Shop - 2/3/2007)
5. Interview/Fear with Flying (Live on The Mike Douglas Show - 4/25/1978)
6. A Father and a Son (Live on ABC Nightline - 6/22/2005)
7. IDTTYWLM (Live on Carrott Confidential, BBC - 2/14/1987)

Disc 1, Tracks 1-3 from Loudon Wainwright III (Atlantic, 1970)
Disc 1, Tracks 4-5 from Album II (Atlantic, 1971)
Disc 1, Tracks 6-8 from Album III (Atlantic, 1972)
Disc 1, Tracks 9-12 from Attempted Mustache (Columbia, 1973)
Disc 1, Tracks 13-15 from Unrequited (Columbia, 1975)
Disc 1, Tracks 16-17 from T Shirt (Arista, 1976)
Disc 1, Tracks 18-20 from Final Exam (Arista, 1978)
Disc 1, Tracks 21-22 from A Live One (Rounder, 1979)
Disc 1, Tracks 23-24 and Disc 2, Track 1 from Fame and Wealth (Rounder, 1983)
Disc 2, Tracks 2-3 from I'm Alright (Rounder, 1985)
Disc 2, Tracks 4-7 from More Love Songs (Rounder, 1986)
Disc 2, Tracks 8-11 from Therapy (Silvertone, 1989)
Disc 2, Tracks 12-15 from History (Charisma, 1992)
Disc 2, Tracks 16-19 from Career Moves (Virgin, 1993)
Disc 2, Tracks 20-22 from Grown Man (Virgin, 1995)
Disc 3, Tracks 1-4 from Little Ship (Virgin, 1996)
Disc 3, Track 5 from BBC Sessions (Strange Fruit, 1998)
Disc 3, Tracks 6-7 from Social Studies (Hannibal, 2000)
Disc 3, Tracks 8-10 from Last Man on Earth (Red House, 2001)
Disc 3, Tracks 11-12 from So Damn Happy (Sanctuary, 2003)
Disc 3, Tracks 13-15 from Here Come the Choppers (Sovereign, 2005)
Disc 3, Tracks 16-17 from Strange Weirdos: Music from and Inspired by the Film Knocked Up (Concord, 2007)
Disc 3, Tracks 18-19 from Recovery (Yep Roc, 2008)
Disc 3, Tracks 20-22 from High Wide & Handsome: The Charlie Poole Project (2nd Story, 2009)