Inkwell Isle I
04:13 - Forest Follies [Run 'n Gun] - P Rank
05:39 - Treetop Trouble [Run 'n Gun] - P Rank
08:59 - Botanic Panic! [The Root Pack] - S Rank
11:30 - Clip Joint Calamity [Ribby and Croaks] - S Rank
14:22 - Mausoleum I
16:24 - Ruse Of An Ooze [Goopy Le Grande] - S Rank
19:23 - Threatenin' Zeppelin [Hilda Berg] - S Rank
22:06 - Floral Fury [Cagney Carnation] - S Rank

Inkwell Isle II
27:07 - Pyramid Peril [Djimmi the Great] - S Rank
30:10 - Carnival Kerfuffle [Beppi the Clown] - S Rank
32:46 - Funhouse Frazzle [Run 'n Gun] - P Rank
34:43 - Fiery Frolic [Grim Matchstick] - S Rank
37:01 - Mausoleum II
39:31 - Sugarland Shimmy [Baroness Von Bon Bon] - S Rank
44:25 - Funfair Fever [Run 'n Gun] - P Rank
45:59 - Aviary Action! [Wally Warbles] - S Rank

Inkwell Isle III
49:45 - Honeycomb Herald [Rumor Honeybottoms] - S Rank
51:53 - Rugged Ridge [Run 'n Gun] - P Rank
54:28 - Junkyard Jive! [Dr. Kahl's Robot] - S Rank
58:30 - Mausoleum III
1:00:17 - Murine Corps [Werner Werman] - S Rank
1:02:35 - Dramatic Fanatic [Sally Stageplay] - S Rank
1:05:35 - Shootin N' Lootin [Captain Brineybeard] - S Rank
1:08:22 - Perilous Piers [Run 'n Gun] - P Rank
1:11:17 - High Seas Hi-Jinx! [Cala Maria] - S Rank
1:14:07 - Railroad Wrath [Phantom Express] - S Rank

Inkwell Hell
1:18:00 - All Bets Are Off! [King Dice] - S Rank
1:23:28 - One Hell Of A Time [The Devil] - S Rank

Inkwell Isle IV [DLC The Delicious Last Course]
1:42:55 - The Pawns [The King's Leap]
1:44:01 - Bootlegger Boogie [Moonshine Mob] - S Rank
1:47:26 - The Knight [The King's Leap]
1:49:15 - High-Noon Hoopla [Esther Winchester] - S Rank
1:52:05 - The Bishop [The King's Leap]
1:53:45 - Gnome Way Out [Glumstone The Giant] - S Rank
1:56:35 - The Rook [The King's Leap]
1:58:50 - Snow Cult Scuffle [Mortimer Freeze] - S Rank
2:01:45 - The Queen [The King's Leap]
2:03:44 - Doggone Dogfight [The Howling Aces] - S Rank
2:07:09 - The Gauntlet [The King's Leap]
2:14:02 - A Dish To Die For [Chef Saltbaker] - S Rank
2:26:23 - One Hell Of A Dream [Angel and Demon]

Note 1: The video does not show the Parry Persistance and Parry Performance achievements for 20 and 100 parries, respectively. You will unlock them as you play.

Inkwell Isle I
03:18 - Coin [1/40]
03:36 - Coin [2-4/40]
04:13 - Coin [5-9/40]
05:34 - Achievement Cutting Corners
05:39 - Coin [10-14/40]
10:33 - Achievement Perfect Run
10:33 - Achievement Taking Names
10:33 - Achievement Put On a Show
13:36 - Achievement Ceramic Strike
24:09 - Achievement A Walk in the Park
24:09 - Achievement Sheriff
25:03 - Coin [15/40]

Inkwell Isle II
32:40 - Coin [16/40]
32:46 - Coin [17-21/40]
37:55 - Achievement Bouncing Ball
38:37 - Coin [22/40]
41:53 - Coin [23/40]
44:25 - Coin [24-28/40]
47:53 - Achievement A Day at the Fair
47:53 - Achievement Boss

Inkwell Isle III
51:53 - Coin [29-33/40]
56:23 - Achievement Porcelain Power
59:33 - Achievement Magician Lord
1:08:22 - Coin [34-38/40]
1:09:50 - Achievement Coffers Full
1:09:50 - Achievement Pacifist
1:11:08 - Coin [39/40]
1:16:11 - Achievement A Trip Downtown
1:16:11 - Achievement Mayor

Inkwell Hell
1:16:55 - Coin [40/40]
1:16:55 - Achievement High Roller
1:17:24 - Achievement Butter-and-Egg Man
1:21:59 - Achievement Rolling Sixes
1:21:59 - Achievement Casino Night
1:23:20 - Achievement Selling Out
1:25:35 - Achievement Swing You Sinner
1:25:35 - Achievement King
1:25:35 - Achievement Beat The Devil At His Own Game
1:27:17 - Achievement Souls Saved

Bravo Zulu P-26
1:31:05 - Achievement Bravo Zulu P-26

Inkwell Isle IV [The Delicious Last Course DLC]
1:40:58 - Coin [1-3/16]
1:41:30 - Coin [4/16]
1:42:00 - Coin [5/40]
1:43:34 - Coin [6-7/16]
1:46:04 - Achievement Alive and Kicking
1:46:04 - Achievement Cooked to Perfection
1:48:56 - Coin [8-9/16]
1:53:24 - Coin [10-11/16]
1:57:59 - Coin [12-13/16]
2:00:53 - Achievement The Latest Sensation
2:02:48 - Achievement Checkmate
2:03:01 - Coin [14-16/16]
2:05:43 - Achievement A Vacation in the Wilds
2:12:23 - Achievement A King's Admiration
2:16:42 - Achievement Compliments to the Chef
2:16:42 - Achievement Ranger
2:27:13 - Achievement A Horrible Night To Have a Curse

Decadent
2:28:09 - Achievement Decadent [Boss 7/10]
2:29:24 - Achievement The Golden Touch
2:29:50 - Achievement Decadent [Boss 8/10]
2:31:18 - Achievement Decadent [Boss 9/10]
2:33:48 - Achievement Decadent [Boss 10/10]
2:35:10 - Achievement Decadent

Hearty
2:36:25 - Achievement Hearty

Paladin
2:38:58 - The Devil [Paladin Points 1-4/16]
2:41:26 - Cala Maria [Paladin Points 5-7/16]
2:43:48 - Dr. Kahl's Robot [Paladin Points 8-10/16]
2:46:07 - Sally Stageplay [Paladin Points 11-13/16]
2:48:08 - Captain Brineybeard [Paladin Points 14-16/16]
2:49:58 - Achievement Paladin

The High Hat
2:50:35 - Achievement The High Hat

Note 2: you can also unlock a new look for Miss Chalice if you defeat all the bosses while playing as her, then go back to island 4 and talk to Cactus Girl., but I didn't stretch the video given that you don't need an S Rank for her.