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

                           PROSPECTUS SUPPLEMENT NO. 2
                     (To Prospectus dated December 29, 2003)

                          21st Century Holding Company

                           816,100 Redeemable Warrants
                         612,075 Shares of Common Stock

      This Prospectus  Supplement  supplements  and amends the Prospectus  dated
December 18, 2003 (the "Prospectus") and Prospectus Supplement dated January 17,
2006  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 and Prospectus  Supplement No.
1, which is to be delivered with this Prospectus Supplement No. 2.

      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 January 25, 2006.



                                    OVERVIEW

      The  Warrants are listed for trading on the NASDAQ  National  Market under
the symbol "TCHCW." On January 24, 2006, the closing sales price of the Warrants
on the NASDAQ  National  Market  ("NASDAQ") was $4.75 per Warrant.  Each Warrant
entitles  the  holder to  purchase  3/4 of one share of our  common  stock at an
exercise  price of $12.744 per whole  share.  On January 24,  2006,  the closing
sales  price of Shares of the  Company's  common  stock on NASDAQ was $18.99 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  and
Prospectus  Supplement No. 1. The information  below presents  information as of
January 24, 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.  Except  for  Omega  Overseas
Partners,  Ltd.  ("Omega")  and Chris  Pellegrini,  each Selling  Securityholder
purchased its Warrants together with a 6% subordinated note ("Note") in our July
2003 private offering of Notes and Warrants.  Omega and Mr. Pellegrini purchased
the Warrants in the open-market,  subsequently exercised the Warrants and we are
registering the resale of the underlying Shares in this Prospectus Supplement.


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                                             Ownership of                              Ownership of
                                              Securities              Number            Securities
                                            Before Offering         Offered By        After Offering
                                       ------------------------      Selling      ----------------------
Selling Securityholder                    Number      Percent       Shareholder
-----------------------------------    -----------  -----------     -----------   ----------------------
                                                                                  
Chris Pellegrini                           3,400           *            3,400           400         *
Newport Alternative Income Fund(1)         6,082           *            6,082             0         *
Omicron Master Trust                     196,098        2.59%          39,235       156,863      2.07%
Omega Overseas Partners, Ltd.             82,500        1.09%          82,500             0         *
OTAPE Investments LLC (1)                 19,617           *           19,617             0         *
SilverCreek II Limited (1)                16,818           *           16,818             0         *
SilverCreek Limited Partnership (1)       37,917           *           37,917             0         *


----------
*     Less than 1%.
(1)   Represents  shares of the Company's common stock underlying  Warrants held
      by certain Selling Securityholders and the number of Warrants held by each
      Selling  Securityholder is as follows:  Newport  Alternative Income Fund -
      8,109 Warrants;  OTAPE  Investments LLC -26,157  Warrants;  SilverCreek II
      Limited,  22,424  Warrants and  SilverCreek  Limited  Partnership - 50,556
      Warrants.

      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:

      o Omega Overseas has appointed John Lattanzio as a manager of a portion of
its investment portfolio. Mr. Lattanzio is responsible for exercising voting and
dispositive  power of the Warrants and the  underlying  Shares of the  Company's
common  stock.  Omega  Advisors,  Inc.  ("Omega  Advisors")  also  serves  as an
investment  advisor to Omega  Overseas.  Leon  Cooperman  is the  President  and
majority  shareholder  of Omega  Advisors;  however,  Mr.  Cooperman  and  Omega
Advisors  disclaim  any voting or  dispositive  power over the  Warrants and the
underlying  Shares of the Company's  common stock because Mr. Lattanzio has been
granted sole voting and  dispositive  power over the portion of Omega  Overseas'
portfolio which includes the Warrants and Shares of the Company's  common stock.
Mr. Cooperman is the managing member of Omega Associates,  L.L.C.,  which is the
general  partner of Omega  Equity  Investors,  L.P  ("Omega  Equity")  and Omega
Capital  Investors,  L.P ("Omega  Capital") and is deemed to exercise voting and
dispositive  control of each of these  entities.  Omega Equity and Omega Capital
each own  270,600  shares  and  50,000  shares of the  Company's  common  stock,
respectively.  Mr. Cooperman is the managing member of Omega Associates, L.L.C.,
which is the general partner of these partnerships.


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      o  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.

      o OTAPE  Investments LLC is wholly-owned by OTA Financial Group, LLC ("OTA
Financial").  Ira Levanthal,  through affiliated entities, serves as the general
partner of OTA Financial and is deemed to have voting and  dispositive  power of
the shares beneficially owned by OTAPE Investments LLC.

      o Each of Newport  Alternative  Income  Fund,  SilverCreek  II Limited and
SilverCreek  Limited  Partnership  is managed by  SilverCreek  Management,  Inc.
Louise  Morwick  and  Bryn  Joynt  are the  managing  members  of  Silver  Creek
Management,  Inc. and have voting and dispositive power over the shares owned by
each of the 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;


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      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 the Prospectus
            and any prospectus supplements;

      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.

      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.


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