FORM 4
[ ] Check this box if no longer subject to Section 16. Form 4 or Form 5 obligations may continue. See Instruction 1(b).         
UNITED STATES SECURITIES AND EXCHANGE COMMISSION
Washington, D.C. 20549

STATEMENT OF CHANGES IN BENEFICIAL OWNERSHIP OF SECURITIES
                                                                                  
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Filed pursuant to Section 16(a) of the Securities Exchange Act of 1934, Section 17(a) of the Public
Utility Holding Company Act of 1935 or Section 30(f) of the Investment Company Act of 1940
                      

1. Name and Address of Reporting Person *

SIMBERG BRUCE 		2. Issuer Name and Ticker or Trading Symbol

21ST CENTURY HOLDING CO [ TCHC ] 		5. Relationship of Reporting Person(s) to Issuer (Check all applicable)

__ X __ Director                      _____ 10% Owner
_____ Officer (give title below)      __ X __ Other (specify below)
Chairman of the Board
(Last)          (First)          (Middle)

3661 WEST OAKLAND PARK BLVD, SUITE 300 		3. Date of Earliest Transaction (MM/DD/YYYY)

12/8/2011
(Street)

LAUDERDALE LAKES, FL 33311
(City)        (State)        (Zip)
4. If Amendment, Date Original Filed (MM/DD/YYYY)

 
6. Individual or Joint/Group Filing (Check Applicable Line)

_ X _ Form filed by One Reporting Person
___ Form filed by More than One Reporting Person

Table I - Non-Derivative Securities Acquired, Disposed of, or Beneficially Owned
1.Title of Security
(Instr. 3) 		2. Trans. Date 2A. Deemed Execution Date, if any 3. Trans. Code
(Instr. 8) 		4. Securities Acquired (A) or Disposed of (D)
(Instr. 3, 4 and 5) 		5. Amount of Securities Beneficially Owned Following Reported Transaction(s)
(Instr. 3 and 4) 		6. Ownership Form: Direct (D) or Indirect (I) (Instr. 4) 7. Nature of Indirect Beneficial Ownership (Instr. 4)
Code V Amount (A) or (D) Price
Common Stock   12/8/2011     P    2648   A $2.72   229477   D    
Common Stock   12/8/2011     P    100   A $2.73   229577   D    

Table II - Derivative Securities Beneficially Owned ( e.g. , puts, calls, warrants, options, convertible securities)
1. Title of Derivate Security
(Instr. 3) 		2. Conversion or Exercise Price of Derivative Security 3. Trans. Date 3A. Deemed Execution Date, if any 4. Trans. Code
(Instr. 8) 		5. Number of Derivative Securities Acquired (A) or Disposed of (D)
(Instr. 3, 4 and 5) 		6. Date Exercisable and Expiration Date 7. Title and Amount of Securities Underlying Derivative Security
(Instr. 3 and 4) 		8. Price of Derivative Security
(Instr. 5) 		9. Number of derivative Securities Beneficially Owned Following Reported Transaction(s) (Instr. 4) 10. Ownership Form of Derivative Security: Direct (D) or Indirect (I) (Instr. 4) 11. Nature of Indirect Beneficial Ownership (Instr. 4)
Code V (A) (D) Date Exercisable Expiration Date Title Amount or Number of Shares
Options   $15.79                    12/5/2006   (1) 12/5/2011   Common Stock   10000     10000   D    
Options   $13.17                    12/6/2008   (1) 12/6/2013   Common Stock   500     500   D    
Options   $12.58                    1/30/2009   (1) 1/30/2014   Common Stock   4500     4500   D    
Options   $4.73                    1/2/2010   (2) 1/2/2019   Common Stock   25000     25000   D    
Options   $2.45                    8/22/2012   (2) 8/22/2021   Common Stock   10000     10000   D    

Explanation of Responses:
( 1)  The options vest 20% per year.
( 2)  The options vest 33 1/3% per year.

Reporting Owners
Reporting Owner Name / Address
Relationships
Director 10% Owner Officer Other
SIMBERG BRUCE
3661 WEST OAKLAND PARK BLVD
SUITE 300
LAUDERDALE LAKES, FL 33311 		X

Chairman of the Board

Signatures
Bruce Simberg 12/12/2011
** Signature of Reporting Person Date


Reminder: Report on a separate line for each class of securities beneficially owned directly or indirectly.
* If the form is filed by more than one reporting person, see Instruction 4(b)(v).
** Intentional misstatements or omissions of facts constitute Federal Criminal Violations. See 18 U.S.C. 1001 and 15 U.S.C. 78ff(a).
Note: File three copies of this Form, one of which must be manually signed. If space is insufficient, see Instruction 6 for procedure.
Persons who respond to the collection of information contained in this form are not required to respond unless the form displays a currently valid OMB control number.
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