Songbook is a 1999 career retrospective album containing 88 songs on four CDs covering Lightfoot's career, and including 16 previously unreleased tracks. The only material not covered are the albums Harmony and Solo, which were released after Songbook.

Slipcase has a dinted corner and some marks on the back.

• 1-1 Remember Me (I'm The One)
• 1-10 Go-Go Round
• 1-11 Crossroads
• 1-12 You'll Still Be Needing Me
• 1-13 The Mountains And Maryann
• 1-14 The Last Time I Saw Her
• 1-15 Did She Mention My Name
• 1-16 Pussywillows Cat-Tails
• 1-17 Boss Man
• 1-18 Something Very Special
• 1-19 Bitter Green
• 1-2 It's Too Late, He Wins
• 1-20 Affair On Eighth Avenue
• 1-21 Medley: I'm Not Sayin' / Ribbon Of Darkness
• 1-22 Softly
• 1-23 Mama Said
• 1-24 Station Master
• 1-3 For Lovin' Me
• 1-4 Early Morning Rain
• 1-5 The Way I Feel
• 1-6 Steel Rail Blues
• 1-7 A Message To The Wind
• 1-8 Song For A Winter's Night
• 1-9 Canadian Railroad Trilogy
• 2-1 Sit Down Young Stranger
• 2-10 Nous Vivons Ensemble
• 2-11 Same Old Loverman
• 2-12 Heaven Don't Deserve Me
• 2-13 Don Quixote
• 2-14 Alberta Bound
• 2-15 Beautiful
• 2-16 Ode To Big Blue
• 2-17 Stone Cold Sober
• 2-18 Old Dan's Records
• 2-19 That Same Old Obsession
• 2-2 If You Could Read My Mind
• 2-20 Lazy Morning
• 2-21 Hi'way Songs
• 2-22 Can't Depend On Love
• 2-3 Poor Little Allison
• 2-4 The Pony Man
• 2-5 Cobwebs & Dust
• 2-6 Too Much To Lose
• 2-7 Summer Side Of Life
• 2-8 Cotton Jenny
• 2-9 Ten Degrees And Getting Colder
• 3-1 Sundown
• 3-10 Summertime Dream
• 3-11 The Wreck Of The Edmund Fitzgerald
• 3-12 Never Too Close
• 3-13 Betty Called Me In
• 3-14 Endless Wire
• 3-15 The Circle Is Small
• 3-16 Sea Of Tranquility
• 3-17 Make Way For The Lady
• 3-18 Dream Street Rose
• 3-19 Ghosts Of Cape Horn
• 3-2 Carefree Highway
• 3-20 Keepin' On Yearnin
• 3-21 Canary Yellow Canoe
• 3-3 Seven Island Suite
• 3-4 Borderstone
• 3-5 Cold On The Shoulder
• 3-6 Now And Then
• 3-7 Rainy Day People
• 3-8 Fine As Fine Can Be
• 3-9 All The Lovely Ladies
• 4-1 Shadows
• 4-10 Broken Dreams
• 4-11 Always On The Bright Side
• 4-12 Forgive Me Lord
• 4-13 Lifeline
• 4-14 East Of Midnight
• 4-15 Morning Glory
• 4-16 A Lesson In Love
• 4-17 A Passing Ship
• 4-18 Waiting For You
• 4-19 Drink Yer Glasses Empty
• 4-2 She's Not The Same
• 4-20 I'll Prove My Love
• 4-21 A Painter Passing Through
• 4-3 14 Karat Gold
• 4-4 Baby Step Back
• 4-5 In My Fashion
• 4-6 Never Say Trust Me
• 4-7 Why Should I Feel Blue
• 4-8 Someone To Believe In
• 4-9 Romance