As far as the Chilly Willy sequencing goes, they are chronological. The first two cartoons continue the sequencing from the first set, but after that, they cherry picked three of the better cartoons from the 60s. While the quality generally declined pretty fast as the Chilly Willy series progressed, the most notable exception, IMHO, is "Half-Baked Alaska", which is very funny, and possibly my favorite cartoon on this set.
Here is a list of the complete contents:
Disc One:
- Woody Woodpecker
- Termites from Mars (12/8/52)
- What's Sweepin' (1/5/53)
- Buccaneer Woodpecker (4/20/53)
- Operation Sawdust (6/15/53)
- Wrestling Wrecks (7/20/53)
- Belle Boys (9/14/53)
- Hypnotic Hick (9/26/53)
- Hot Noon (10/12/53)
- Socko in Morocco (1/18/54)
- Alley to Bali (3/15/54)
- Under the Counter Spy (5/10/54)
- Hot Rod Huckster (7/5/54)
- Real Gone Woody (9/20/54)
- A Fine Feathered Frenzy (10/25/54)
- Convict Concerto (11/20/54)
- Oswald the Lucky Rabbit
- Carnival Capers (10/10/32)
- Five and Dime (9/18/33)
- Wax Works (6/25/34)
- Springtime Serenade (5/27/35)
- Puppet Show (11/11/36)
- Cartune Classics
- She Done Him Right (10/9/33)
- Jolly Little Elves (10/1/34)
- Candyland (4/22/35)
- A Haunting We Will Go (9/4/39)
- Fair Today (2/24/41)
Disc Two:
- Woody Woodpecker
- Helter Shelter (1/17/55)
- Witch Crafty (3/14/55)
- Private Eye Pooch (5/9/55)
- Bedtime Bedlam (7/4/55)
- Square Shootin' Square (9/1/55)
- Bunco Busters (11/21/55)
- The Tree Medic (12/9/55)
- After the Ball (2/13/56)
- Get Lost (3/12/56)
- Chief Charlie Horse (5/7/56)
- Woodpecker from Mars (7/2/56)
- Calling All Cuckoos (9/24/56)
- Niagara Fools (10/22/56)
- Arts and Flowers (11/19/56)
- Woody Meets Davy Crewcut (12/17/56)
- Andy Panda
- 100 Pygmies and Andy Panda (4/22/40)
- The Painter and the Pointer (12/18/44)
- The Poet and Peasant (3/18/46)
- Mousie Come Home (4/15/46)
- Dog Tax Dodgers (11/26/48)
- Musical Favorites
- Three Hams That Couldn't Be Cured (3/4/42)
- Juke Box Jamboree (7/27/42)
- Boogie Woogie Man (9/27/43)
- The Overture to William Tell (6/16/47)
- Pixie Picnic (5/1/48)
Disc Three:
- Woody Woodpecker
- Red Riding Hoodlum (2/11/57)
- Box Car Bandit (4/8/57)
- The Unbearable Salesman (6/3/57)
- International Woodpecker (7/1/57)
- To Catch a Woodpecker (7/29/57)
- Round Trip to Mars (9/23/57)
- Dopey Dick the Pink Whale (11/1/57)
- Fodder and Son (11/4/57)
- Misguided Missile (1/27/58)
- Watch the Birdie (2/24/58)
- Half Empty Saddles (4/21/58)
- His Better Elf (7/14/58)
- Everglade Raid (8/11/58)
- Tree's a Crowd (9/8/58)
- Jittery Jester (11/3/58)
- Chilly Willy
- Hold That Rock (7/30/56)
- Operation Cold Feet (5/6/57)
- Clash and Carry (4/26/61)
- Deep Freeze Squeeze (3/1/64)
- Half Baked Alaska (4/1/65)
- Cartune Co-Stars
- Maw and Paw (8/10/53)
- A Horse's Tale (2/15/54)
- Dig That Dog (4/12/54)
- The Ostrich Egg and I (4/9/56)
- Salmon Yeggs (3/24/58)