UNITED STATES
                       SECURITIES AND EXCHANGE COMMISSION
                             WASHINGTON, D.C. 20549


                                    FORM 8-K

                                 CURRENT REPORT

                     Pursuant to Section 13 or 15(d) of the
                         Securities Exchange Act of 1934


                         Date of Report: April 29, 2005
                        (Date of earliest event reported)


                          21ST CENTURY HOLDING COMPANY
             (Exact name of registrant as specified in its charter)


            Florida                       0-2500111              65-0248866
--------------------------------  ------------------------  --------------------
(State or other jurisdiction of   (Commission File Number)    (I.R.S. Employer
         incorporation)                                      Identification No.)


        3661 West Oakland Park Blvd., Suite 300
                 Lauderdale Lakes, FL                           33311
   ----------------------------------------------------   ------------------
       (Address of principal executive offices)              (Zip Code)

       Registrant's telephone number, including area code: (954) 581-9993
                                                           --------------

                                 NOT APPLICABLE
          -------------------------------------------------------------
          (Former Name or Former Address, if Changed Since Last Report)

Check  the  appropriate  box  below  if the  Form  8-K  filing  is  intended  to
simultaneously  satisfy the filing obligation of the registrant under any of the
following provisions (see General Instruction A.2. below):

      |_|   Written communications pursuant to Rule 425 under the Securities Act
            (17 CFR 230.425)

      |_|   Soliciting  material  pursuant to Rule 14a-12 under the Exchange Act
            (17 CFR 240.14a-12)

      |_|   Pre-commencement  communications pursuant to Rule 14d-2(b) under the
            Exchange Act (17 CFR 240.14d-2(b))


      |_|   Pre-commencement  communications pursuant to Rule 13e-4(c) under the
            Exchange Act (17 CFR 240.13e-4(c))

<PAGE>

Item 2.04   Triggering  Events that  Accelerate  or Increase a Direct  Financial
            Obligation or an Obligation under an Off-Balance-Sheet Arrangement

      On April 29, 2005, 21st Century  Holding Company (the "Company")  received
from  counsel  to  Whitebox  Advisors  ("Whitebox"),  the  beneficial  owner  of
approximately $8.7 million in outstanding  principal balance of the Company's 6%
Senior Subordinated Notes (the "Notes"),  a letter alleging the Company's breach
of the purchase  agreements between the Company and the purchasers of the Notes.
The allegation relates to the Company's  withdrawal of a previously given notice
to the Note holders,  which stated that the Company elected to pay the April 30,
2005  payment  of  principal  and  interest  due on the  Notes in  shares of the
Company's  common  stock.  Note  holders'  remedies  with respect to an event of
default include  acceleration of the outstanding  principal amount of Notes due,
which as of the date of this Report totaled $15.2 million,  and such other legal
or  equitable  relief  to which the Note  holders  may  prove  themselves  to be
entitled.  The Company  timely  made the April 30, 2005  payment due to the Note
holders in full, in cash. The Company  believes that the payment in cash and the
withdrawal  of  the  notice  is  consistent  with  the  terms  of  the  purchase
agreements, and that no event of default under the purchase agreements exists.

      As of the date of this  Report,  the Company and  Whitebox  have reached a
verbal  agreement,  whereby  Whitebox  agreed to accept the April 30,  2005 cash
payment  in  exchange  for  the  Company's  agreement  to  refrain  from  future
withdrawals of the notice of intention to pay in shares.  The Company has had no
contact from any other Note holders and believes that this matter is resolved.

<PAGE>


SIGNATURES

      Pursuant to the  requirements of the Securities  Exchange Act of 1934, the
registrant  has duly  caused  this  report  to be  signed  on its  behalf by the
undersigned hereunto duly authorized.


                                    21ST CENTURY HOLDING COMPANY


Date: May 5, 2005                   By:  /s/ Richard A. Widdicombe
                                        ----------------------------------------
                                    Name:    Richard A. Widdicombe
                                    Title:   Chief Executive Officer
                                             (Principal Executive Officer)

Date: May 5, 2005                   By:  /s/ J. Gordon Jennings III
                                        ----------------------------------------
                                    Name:    J. Gordon Jennings III
                                    Title:   Chief Financial Officer
                                    (Principal Accounting and Financial Officer)
{"company-data": {"conformed-name": "21ST CENTURY HOLDING CO", "cik": "0001069996", "assigned-sic": "6331", "irs-number": "650248866", "state-of-incorporation": "FL", "fiscal-year-end": "1231"}, "filing-values": {"form-type": "8-K", "act": "34", "file-number": "000-25001", "film-number": "05803798"}, "business-address": {"street1": "4161 N W 5TH STREET", "city": "PLANTATION", "state": "FL", "zip": "33317", "phone": "9545819993"}, "mail-address": {"street1": "4161 N W 5TH STREET", "city": "PLANTATION", "state": "FL", "zip": "33317"}}
UNITED STATES
                       SECURITIES AND EXCHANGE COMMISSION
                             WASHINGTON, D.C. 20549

                                    FORM 8-K

                                 CURRENT REPORT

                     Pursuant to Section 13 or 15(d) of the
                         Securities Exchange Act of 1934

                         Date of Report: April 29, 2005
                        (Date of earliest event reported)

                          21ST CENTURY HOLDING COMPANY
             (Exact name of registrant as specified in its charter)

            Florida                       0-2500111              65-0248866
--------------------------------  ------------------------  --------------------
(State or other jurisdiction of   (Commission File Number)    (I.R.S. Employer
         incorporation)                                      Identification No.)

        3661 West Oakland Park Blvd., Suite 300
                 Lauderdale Lakes, FL                           33311
   ----------------------------------------------------   ------------------
       (Address of principal executive offices)              (Zip Code)

       Registrant's telephone number, including area code: (954) 581-9993
                                                           --------------

                                 NOT APPLICABLE
          -------------------------------------------------------------
          (Former Name or Former Address, if Changed Since Last Report)

Check  the  appropriate  box  below  if the  Form  8-K  filing  is  intended  to
simultaneously  satisfy the filing obligation of the registrant under any of the
following provisions (see General Instruction A.2. below):

      |_|   Written communications pursuant to Rule 425 under the Securities Act
            (17 CFR 230.425)

      |_|   Soliciting  material  pursuant to Rule 14a-12 under the Exchange Act
            (17 CFR 240.14a-12)

      |_|   Pre-commencement  communications pursuant to Rule 14d-2(b) under the
            Exchange Act (17 CFR 240.14d-2(b))

      |_|   Pre-commencement  communications pursuant to Rule 13e-4(c) under the
            Exchange Act (17 CFR 240.13e-4(c))
Item 2.04   Triggering  Events that  Accelerate  or Increase a Direct  Financial
            Obligation or an Obligation under an Off-Balance-Sheet Arrangement

      On April 29, 2005, 21st Century  Holding Company (the "Company")  received
from  counsel  to  Whitebox  Advisors  ("Whitebox"),  the  beneficial  owner  of
approximately $8.7 million in outstanding  principal balance of the Company's 6%
Senior Subordinated Notes (the "Notes"),  a letter alleging the Company's breach
of the purchase  agreements between the Company and the purchasers of the Notes.
The allegation relates to the Company's  withdrawal of a previously given notice
to the Note holders,  which stated that the Company elected to pay the April 30,
2005  payment  of  principal  and  interest  due on the  Notes in  shares of the
Company's  common  stock.  Note  holders'  remedies  with respect to an event of
default include  acceleration of the outstanding  principal amount of Notes due,
which as of the date of this Report totaled $15.2 million,  and such other legal
or  equitable  relief  to which the Note  holders  may  prove  themselves  to be
entitled.  The Company  timely  made the April 30, 2005  payment due to the Note
holders in full, in cash. The Company  believes that the payment in cash and the
withdrawal  of  the  notice  is  consistent  with  the  terms  of  the  purchase
agreements, and that no event of default under the purchase agreements exists.

      As of the date of this  Report,  the Company and  Whitebox  have reached a
verbal  agreement,  whereby  Whitebox  agreed to accept the April 30,  2005 cash
payment  in  exchange  for  the  Company's  agreement  to  refrain  from  future
withdrawals of the notice of intention to pay in shares.  The Company has had no
contact from any other Note holders and believes that this matter is resolved.
SIGNATURES

      Pursuant to the  requirements of the Securities  Exchange Act of 1934, the
registrant  has duly  caused  this  report  to be  signed  on its  behalf by the
undersigned hereunto duly authorized.

                                    21ST CENTURY HOLDING COMPANY

Date: May 5, 2005                   By:  /s/ Richard A. Widdicombe
                                        ----------------------------------------
                                    Name:    Richard A. Widdicombe
                                    Title:   Chief Executive Officer
                                             (Principal Executive Officer)

Date: May 5, 2005                   By:  /s/ J. Gordon Jennings III
                                        ----------------------------------------
                                    Name:    J. Gordon Jennings III
                                    Title:   Chief Financial Officer
                                    (Principal Accounting and Financial Officer)