Forty one years after first performing in the Big Yard, Hollis "Chalkdust" Liverpool delivered a preformance described by a patron as "he mash up the place" to take the 2009 Calypso Monarch title. His song "My Heart and I" filled with "picong" about the on-going divide between the Prime Minister and Dr. Keith Rowley won the hearts of the judges at the Queen's Park Savannah and to the delight of the crowd gained him his 8th Calypso Monarch Title.

The win for Chalkdust has equalled that of The Calypso King of the World Slinger "The Mighty Sparrow" Francisco for the accolade of most ever Calypso Monarch crowns.

2009 Calypso Monarch results

1st place
Chalkdust (Dr. Hollis Liverpool) 434 points
Song: My heart and I

2nd place
Tigress (Joanne Rowley) 426 points
Song: Yuh Ent See Wajang Yet

3rd place
The Original De Fosto Himself (Winston Scarborough) 425 points
Song: Could We Rise Again

4th place
Brian London 424 points
Song: A Nation's Son

5th place
Kizzie Ruiz 414 points
Song: Class Language

6th place
Singing Sandra (Sandra Des Vignes-Millington) 412 points
Song: Ghetto of Your Mind

7th place Tie of 409 points
Sugar Aloes (Michael Osouna)
Song: Obama The First

Twiggy (Ann Marie Parks Kojo )
Song: One for Obama

Gypsy (Winston Peters)
Song: Supply and Demand

10th place
Karen Asche 401 points
Song: Babylon

11th place
Stinger (Dexter Parsons) 400 points
Song: Our Environmental Engineers

12th place
Skatie (Carlos James) 397 points
Song: On Solid Ground

13th place
All Rounder (Anthony Hendrickson) 396 points
Song: Help Your Children First

14th place
Cro Cro (Weston Rawlins) 396 points
Song: Ah Feeling Shame

15th place
Contender (Mark John) 392 points
Song: Yuh Cyar Buy One

16th place
Bally (Errol Ballantyne) 386 points
Amigo