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: JANUARY 31, 2006
                        (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       (COMMISSION FILE           (I.R.S. EMPLOYER
      OF INCORPORATION)                 NUMBER)              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 CFT 240.13E-4( C))


<PAGE>

ITEM 1.01. ENTRY INTO A MATERIAL DEFINITIVE AGREEMENT

Separation and Release Agreement

On January 31, 2006,  Mr. Kent M. Linder,  the Chief  Operating  Officer of 21st
Century  Holding  Company  (the  "Company"),  and  the  Company  entered  into a
Separation  and Release  Agreement  (the  "Agreement")  under  which Mr.  Linder
resigned from his position as Chief  Operating  Officer  effective as of January
31, 2006, and from all other officer and director positions with the Company and
its subsidiaries.  Set forth below is a description of the material terms of the
Agreement.

Severence  Payment.  Mr.  Linder will receive a severance  payment of Thirty-Six
Thousand Four Hundred Dollars ($36,400.00), in the aggregate, which is comprised
of seven salary payments in the amount of $5,200.00 each through April 30, 2005.
The payments will be made pursuant to the Company's normal payroll schedule.

In exchange, Mr. Linder has agreed to certain covenants prohibiting competition,
solicitation of employees,  non-disparagement  and has provided the Company with
customary releases and acknowledgements.

ITEM 5.02. DEPARTURE OF DIRECTORS OR PRINCIPAL OFFICERS;  ELECTION OF DIRECTORS;
APPOINTMENT OF PRINCIPAL OFFICERS

      Effective as of January 31, 2006,  Kent M. Linder resigned as 21st Century
Holding  Company's  (the  "Company")  Chief  Operating  Officer.  Mr.  Linder is
resigning  for  personal  reasons and does not have any  disagreements  with the
Company.  Mr.  Linder and the  Company  entered  into a  separation  and release
agreement.

      The Company has not appointed a  replacement  Chief  Operating  Officer at
this time.

ITEM 9.01 FINANCIAL STATEMENTS AND EXHIBITS.

(c)         Exhibits.
            ---------
99.1        Separation  and  Release  Agreement  between  21st  Century  Holding
            Company and Kent M. Linder


<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:  January 31, 2006                 By: /s/ JAMES GORDON JENNINGS, III
                                            ----------------------------------
                                        Name:   James Gordon Jennings, III
                                        Title:  Chief Financial Officer
                                               (Principal Accounting and
                                                Financial Officer)


<PAGE>

                                  EXHIBIT INDEX
                                  -------------


EXHIBIT NO.       EXHIBIT TITLE
-----------       -------------

      99.1        Separation and Release  Agreement between 21st Century Holding
                  Company and Kent M. Linder
{"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": "06566308"}, "business-address": {"street1": "3661 WEST OAKLAND PARK BLVD", "street2": "SUITE 300", "city": "LAUDERDALE LAKES", "state": "FL", "zip": "33311", "phone": "9545819993"}, "mail-address": {"street1": "3661 WEST OAKLAND PARK BLVD", "street2": "SUITE 300", "city": "LAUDERDALE LAKES", "state": "FL", "zip": "33311"}}
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: JANUARY 31, 2006
                        (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       (COMMISSION FILE           (I.R.S. EMPLOYER
      OF INCORPORATION)                 NUMBER)              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 CFT 240.13E-4( C))
ITEM 1.01. ENTRY INTO A MATERIAL DEFINITIVE AGREEMENT

Separation and Release Agreement

On January 31, 2006,  Mr. Kent M. Linder,  the Chief  Operating  Officer of 21st
Century  Holding  Company  (the  "Company"),  and  the  Company  entered  into a
Separation  and Release  Agreement  (the  "Agreement")  under  which Mr.  Linder
resigned from his position as Chief  Operating  Officer  effective as of January
31, 2006, and from all other officer and director positions with the Company and
its subsidiaries.  Set forth below is a description of the material terms of the
Agreement.

Severence  Payment.  Mr.  Linder will receive a severance  payment of Thirty-Six
Thousand Four Hundred Dollars ($36,400.00), in the aggregate, which is comprised
of seven salary payments in the amount of $5,200.00 each through April 30, 2005.
The payments will be made pursuant to the Company's normal payroll schedule.

In exchange, Mr. Linder has agreed to certain covenants prohibiting competition,
solicitation of employees,  non-disparagement  and has provided the Company with
customary releases and acknowledgements.

ITEM 5.02. DEPARTURE OF DIRECTORS OR PRINCIPAL OFFICERS;  ELECTION OF DIRECTORS;
APPOINTMENT OF PRINCIPAL OFFICERS

      Effective as of January 31, 2006,  Kent M. Linder resigned as 21st Century
Holding  Company's  (the  "Company")  Chief  Operating  Officer.  Mr.  Linder is
resigning  for  personal  reasons and does not have any  disagreements  with the
Company.  Mr.  Linder and the  Company  entered  into a  separation  and release
agreement.

      The Company has not appointed a  replacement  Chief  Operating  Officer at
this time.

ITEM 9.01 FINANCIAL STATEMENTS AND EXHIBITS.

(c)         Exhibits.
            ---------
99.1        Separation  and  Release  Agreement  between  21st  Century  Holding
            Company and Kent M. Linder
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:  January 31, 2006                 By: /s/ JAMES GORDON JENNINGS, III
                                            ----------------------------------
                                        Name:   James Gordon Jennings, III
                                        Title:  Chief Financial Officer
                                               (Principal Accounting and
                                                Financial Officer)
EXHIBIT INDEX
                                  -------------

EXHIBIT NO.       EXHIBIT TITLE
-----------       -------------

      99.1        Separation and Release  Agreement between 21st Century Holding
                  Company and Kent M. Linder