SEC File No.: 333-109313
                                     Filed pursuant to Rule 424(b)(3) and 424(c)

                           PROSPECTUS SUPPLEMENT NO. 1
                     (To Prospectus dated December 2, 2004)

                          21st Century Holding Company

                          1,019,608 Redeemable Warrants
                        1,088,808 Shares of Common Stock

      This Prospectus  Supplement  supplements  and amends the Prospectus  dated
December 2, 2004 (the "Prospectus") relating to the resales from time to time by
holders (the "Selling  Securityholders") of our Warrants ("Warrants") and Shares
("Shares") of our common stock  issuable  upon  exercise of the  Warrants.  This
Prospectus  Supplement should be read in conjunction with the Prospectus,  which
is to be delivered with this Prospectus Supplement.

      NEITHER THE  SECURITIES  AND EXCHANGE  COMMISSION OR ANY STATE  SECURITIES
COMMISSION HAS APPROVED OR  DISAPPROVED  OF THESE  SECURITIES OR PASSED UPON THE
ADEQUACY OR ACCURACY OF THIS PROSPECTUS  SUPPLMENT.  ANY  REPRESENTATION  TO THE
CONTRARY IS A CRIMINAL OFFENSE.

           The date of this Prospectus Supplement is February 1, 2006.



                                    OVERVIEW

      The  Warrants are listed for trading on the NASDAQ  National  Market under
the symbol "TCHCZ." On January 31, 2006, the closing sales price of the Warrants
on the NASDAQ National Market  ("NASDAQ") was $5.55 per Warrant.  There have not
been any reported  trades of the Warrants since January 9, 2006 through the date
of this  Supplement.  Each Warrant  entitles the holder to purchase one share of
our common stock at an exercise price of $12.75 per whole share.  On January 31,
2006, the closing sales price of Shares of the Company's  common stock on NASDAQ
was $18.50 per share.

                             SELLING SECURITYHOLDERS

      The  information  in  the  table  appearing  under  the  heading  "Selling
Securityholders"  adds information with respect to persons not previously listed
in the  Prospectus as Selling  Securityholders  and supersedes  information  for
persons  previously  listed as Selling  Securityholders  in the Prospectus.  The
information  below  presents  information  as of January 31, 2006  regarding the
Selling  Securityholders  and the  Warrants  and the  Shares  that  the  Selling
Securityholders may offer and sell from time to time under this Prospectus.  The
table  is  prepared  based  on  information   supplied  to  us  by  the  Selling
Securityholders.

      Although we have  assumed for purposes of the table below that the Selling
Securityholders  will  sell  all of the  Warrants  or  Shares  offered  by  this
Prospectus,  no  assurances  can be given as to the actual number of Warrants or
Shares that will be resold by the Selling  Securityholders  or that will be held
by the Selling Securityholders after completion of the resales. In addition, the
Selling  Securityholders may have sold, transferred or otherwise disposed of the
Warrants or the Shares in transactions exempt from the registration requirements
of the  Securities Act since the date the Selling  Securityholders  provided the
information  regarding their  securities  holdings.  Information  concerning the
Selling  Securityholders  may change from time to time and  changed  information
will  be  presented  in a  supplement  to  the  Prospectus  and  the  Prospectus
Supplement if and when necessary and required.

      None of the Selling  Securityholders has been within the last three years,
or is  currently,  affiliated  with the Company.  Each Selling  Security  holder
purchased  its Warrants  together  with a 6%  subordinated  note ("Note") in our
September 2004 private offering of Notes and Warrants.



- ----------------------------------------------------------------------------------------------------------------------
                                                      Ownership of                               Ownership of
                                                       Securities             Number              Securities
                                                     Before Offering        Offered By          After Offering
- -----------------------------------------------------------------------       Selling    -----------------------------
Selling Shareholder                                 Number     Percent      Shareholder       Number     Percent
- ----------------------------------------------------------------------------------------------------------------------
                                                                                           
Corsair Capital Partners, LP (1)                    55,947         *           50,588          5,359         *
- ----------------------------------------------------------------------------------------------------------------------
Corsair Capital Partners 100, LP (1)                 2,169         *            1,961            208         *
- ----------------------------------------------------------------------------------------------------------------------
Corsair Capital Partners Investors, LTD. (1)         6,940         *            6,275            665         *
- ----------------------------------------------------------------------------------------------------------------------
Cranshire Capital, LP (1)                           78,431      1.00%          78,431              0         *
- ----------------------------------------------------------------------------------------------------------------------
Hillson Partners Limited Partnership               261,212      3.20%          78,431        182,781      2.29%
- ----------------------------------------------------------------------------------------------------------------------
Iroquois Capital LP (1)                             78,431      1.00%          78,431              0         *
- ----------------------------------------------------------------------------------------------------------------------
Omicron Master Trust                               104,747      1.31%          65,512         39,235         *
- ----------------------------------------------------------------------------------------------------------------------
Whitebox Convertible Arbitrage Partners, LP        225,619      2.82%         224,619          1,000         *
- ----------------------------------------------------------------------------------------------------------------------
Pandora Select Partners, LP                         45,131         *           45,131              0         *
- ----------------------------------------------------------------------------------------------------------------------
Whitebox Intermarket Partners, LP                   33,824         *           33,824              0         *
- ----------------------------------------------------------------------------------------------------------------------


- ----------
* Less than 1%.

(1) Includes shares  underlying  warrants held by certain  selling  shareholders
(each of which is exercisable for one share of common stock) as follows: Corsair
Capital Partners,  LP, 50,588 warrants;  Corsair Capital Partners 100, LP, 1,961
warrants;  Corsair Capital Partners Investors,  LTD., 6,275 warrants;  Cranshire
Capital, LP, 78,431 warrants; and Iroquois Capital LP, 78,431 warrants.


                                       1


      The Selling  Securityholders listed above have provided us with additional
information  regarding the  individuals  or entities that exercise  control over
each  Selling  Securityholder.  The  proceeds  of any sale of Warrants or Shares
pursuant to the Prospectus and the Prospectus Supplement will be for the benefit
of the individuals that control the selling entity.

      The  following is a list of the Selling  Securityholders  and the entities
that may  exercise  the right to vote or  dispose  of the  shares  owned by each
Selling Securityholder:

            Jay  Petschek,  serves as the  managing  member of  Corsair  Capital
Advisors,  LLC,  the general  partner of Cosair  Capital  Partners,  LP,  Cosair
Capital  Partners  100,  LP and Cosair  Capital  Investors,  Ltd.  Mr.  Petschet
exercises sole voting and dispositive power over these securities.

            Mitchell P. Kopin, is the President of Downsview Capital,  Inc., the
General  Partner  of  Cranshire  Capital,  L.P.  Mr.  Kopin has sole  voting and
dispositive power over the securities held by Cranshire Capital, LP.

            Daniel Abramowitz, is the President of Hillson Financial Management,
Inc.,  the  general  partner  of  Hillson  Partners  Limited  Partnership.   Mr.
Abramowitz has sole voting and  dispositive  power over the  securities  held by
Hillson Partners Limited Partnership.

            Joshua Silverman is a partner of Iroquois Capital, LP. Mr. Silverman
has sole and voting and  dispositive  power over the securities held by Iroquois
Capital, LP.

            Omicron  Capital,  L.P., a Delaware  limited  partnership  ("Omicron
Capital"),  serves as investment manager to Omicron Master Trust, a trust formed
under  the laws of  Bermuda  ("Omicron");  Omicron  Capital,  Inc.,  a  Delaware
corporation  ("OCI"),   serves  as  general  partner  of  Omicron  Capital;  and
Winchester Global Trust Company Limited  ("Winchester") serves as the trustee of
Omicron. By reason of such relationships,  Omicron Capital and OCI may be deemed
to share dispositive power over the shares of our common stock owned by Omicron,
and  Winchester  may be deemed to share  voting and  dispositive  power over the
shares of our common stock owned by Omicron. Omicron Capital, OCI and Winchester
disclaim  beneficial  ownership  of such  shares of our  common  stock.  Omicron
Capital  has  delegated  authority  from the board of  directors  of  Winchester
regarding  the  portfolio  management  decisions  with  respect to the shares of
common  stock owned by Omicron  and, as of December  30,  2005,  Mr.  Olivier H.
Morali and Mr. Bruce T.  Bernstein,  officers of OCI, have  delegated  authority
from the board of directors of OCI regarding the portfolio  management decisions
with respect to the shares of common  stock owned by Omicron.  By reason of such
delegated  authority,  Messrs.  Morali  and  Bernstein  may be  deemed  to share
dispositive power over the shares of our common stock owned by Omicron.  Messrs.
Morali and Bernstein disclaim beneficial  ownership of such shares of our common
stock and neither of such persons has any legal right to maintain such delegated
authority.  No other person has sole or shared voting or dispositive  power with
respect to the shares of our common  stock being  offered by  Omicron,  as those
terms are used for purposes under  Regulation  13D-G of the Securities  Exchange
Act of 1934, as amended.  Omicron and  Winchester  are not  "affiliates"  of one
another,  as that term is used for  purposes of the  Securities  Exchange Act of
1934, as amended,  or of any other person named in this  prospectus as a selling
shareholder.  No person or "group" (as that term is used in Section 13(d) of the
Securities  Exchange Act of 1934,  as amended,  or the SEC's  Regulation  13D-G)
controls Omicron and Winchester.


                                       2


            Mr. Andrew Redleaf is the managing member of the general partner for
Whitebox Convertible  Arbitrage Partners,  LP; Whitebox Intermarket Partners, LP
and Pandora Select Partners, LP. and exercises sole voting and dispositive power
over the securities held by each of these entities.

                              PLAN OF DISTRIBUTION

      The Selling Securityholders and any pledgees, donees, transferees or other
successors in interest of the Selling Securityholders  (collectively,  all shall
be referred to as the  "Selling  Securityholders")  may sell their  Warrants and
Shares in various ways and at various  prices.  Some of the methods by which the
Warrants and the Shares may be sold include:

      o     ordinary brokerage transactions and transactions in which the broker
            solicits  purchasers  or makes  arrangements  for other  brokers  to
            participate in soliciting purchasers;

      o     privately negotiated transactions;

      o     block  trades in which the broker or dealer will attempt to sell the
            Warrants or Shares as agent but may position and resell a portion of
            the block as principal to facilitate the transaction;

      o     purchases  by a broker  or dealer as  principal  and  resale by that
            broker or dealer for the Selling Securityholder's account under this
            prospectus  on the  Nasdaq  National  Market at prices  and on terms
            then-prevailing in the market;

      o     sales  under  Rule  144,  if  available,   rather  than  using  this
            Prospectus;

      o     a combination of any of these methods of sale; and

      o     any other legally permitted method.

The  applicable  sales  price may be  affected  by the type of  transaction.  In
addition, this Plan of Distribution, is also updated to include, the exercise of
the  Warrants by  assignees,  transferees,  purchasers  or other  successors  in
interest to the original Selling Securityholders listed in the Prospectus.

      When selling Warrants and/or Shares, the Selling Securityholders intend to
comply with the prospectus  delivery  requirements  under the Securities Act, by
delivering the Prospectus,  this Prospectus Supplement and any other supplements
or amendments to these documents to each purchaser. We may file any supplements,
amendments or other  necessary  documents in compliance  with the Securities Act
that may be required if a Selling  Securityholder  defaults  under any  customer
agreement with brokers.


                                       3


      Brokers and dealers may receive  commissions or discounts from the Selling
Securityholders  or, if the broker-dealer acts as agent for the purchaser of the
Warrants or Shares,  from that  purchaser,  in amounts to be  negotiated.  These
commissions  are  not  expected  to  exceed  those  customary  in the  types  of
transactions  involved.  We cannot  estimate at the  present  time the amount of
commissions   or   discounts,   if  any,  that  will  be  paid  by  the  Selling
Securityholders in connection with any sales of the Warrants and/or Shares.

      The  Selling   Securityholders  and  any  broker-dealers  or  agents  that
participate  with a  Selling  Securityholders  in sales of the  Warrants  and/or
Shares  may, in certain  instances,  be deemed to be  "underwriters"  within the
meaning of the Securities Act in connection with these sales. In that event, any
commissions  received  by the  broker-dealers  or agents  and any  profit on the
resale  of the  Warrants  or the  Shares  purchased  by them may be deemed to be
underwriting commissions or discounts under the Securities Act.

      Under the securities laws of certain  states,  the Warrants and Shares may
be sold in those states only through registered or licensed  broker-dealers.  In
addition, the Warrants and Shares may not be sold unless the Warrants and Shares
have been  registered or qualified for sale in the relevant  state or unless the
Warrants and Shares qualify for an exemption from registration or qualification.

      We  have  agreed  to  pay  all  of  our  out-of-pocket  expenses  and  our
professional fees and expenses incident to the registration of the resale of the
Warrants and the issuance of the Shares. The Selling  Securityholders  and other
persons  participating  in any  distribution  of the Warrants or Shares  offered
under  this  Prospectus  and  this  Prospectus  Supplement  are  subject  to the
applicable  requirements  of Regulation M promulgated  under the Exchange Act in
connection with sales of the Warrants and the Shares.


                                       4