Exhibit 5

                      Jenkens & Gilchrist Parker Chapin LLP




                                                              AUSTIN, TEXAS
                                                             (512) 499-3800
                            THE CHRYSLER BUILDING           CHICAGO, ILLINOIS
                            405 LEXINGTON  AVENUE            (312) 425-3900
                           NEW YORK, NEW YORK 10174           DALLAS, TEXAS
                                                             (214) 855-4500
                               (212) 704-6000                HOUSTON, TEXAS
                           FACSIMILE (212) 704-6288          (713) 951-3300
                                                         LOS ANGELES, CALIFORNIA
                               www.jenkens.com               (310) 820-8800
                                                           SAN ANTONIO, TEXAS
                                                             (210) 246-5000
                                                            WASHINGTON, D.C.
                                                             (202) 326-1500
                               October 7, 2002


SmartServ Online, Inc.
Metro Center
One Station Place
Stamford, CT 06902

Gentlemen:

         We have  acted  as  counsel  to  SmartServ  Online,  Inc.,  a  Delaware
corporation  (the  "Company"),  in  connection  with the  Company's  filing of a
Registration  Statement  on Form S-3  (the  "Registration  Statement")  with the
Securities and Exchange  Commission (the "Commission")  under the Securities Act
of 1933,  as amended  (the  "Act"),  relating to the resale of an  aggregate  of
45,064 shares (the  "Non-Callable  Warrant  Shares") of Common Stock,  par value
$.01 per share (the "Common Stock"),  of the Company,  issuable upon exercise of
non-callable  warrants (the  "Non-Callable  Warrants")  issued by the Company to
Bonanza Master Fund,  Ltd.  ("Bonanza")  and Vertical  Ventures  Investments LLC
("Vertical";  Bonanza and  Vertical are  collectively  referred to herein as the
"Investors"),  and 84,926 shares of Common Stock issuable upon the triggering of
certain  anti-dilution  provisions  contained in the Non-Callable  Warrants (the
"Anti-Dilution  Shares";  the Non-Callable  Warrant Shares and the Anti-Dilution
Shares are collectively referred to herein as the "Warrant Shares").

         In connection with the foregoing, we have examined originals or copies,
satisfactory  to us, of: (i) the Securities  Purchase  Agreement,  dated May 20,
2002,  as  amended  on  June  5,  2002  (the  "Purchase  Agreement"),  (ii)  the
Non-Callable  Warrants,  (iii) the Company's  Certificate of  Incorporation,  as
amended, (iv) the Company's By-laws, and (vi) resolutions of the Company's board
of  directors  authorizing  the  Company  to enter  into,  and  consummate,  the
transactions  contemplated by the Purchase Agreement,  including the issuance of
the Non-Callable Warrants. We have also reviewed such other matters of law as we
have  deemed  relevant  and  necessary  as a basis for the  opinion  hereinafter
expressed.  In  such  examination,  we  have  assumed  the  genuineness  of  all
signatures,  the authenticity of all documents  submitted to us as originals and
the conformity with the original  documents of all documents  submitted to us as
copies or facsimiles.  As to any facts material to such opinion, we have, to the
extent that relevant facts were not  independently  established by us, relied on
certificates  of  public   officials  and  certificates  of  officers  or  other
representatives of the Company.



                     Jenkens & Gilchrist Parker Chapin LLP

SmartServ Online, Inc.
October 7, 2002
Page 2



         Based upon and subject to the foregoing, we are of the opinion that the
Warrant  Shares,  upon  issuance and payment by the  Investors to the Company in
accordance with the terms of the Non-Callable Warrants,  will be validly issued,
fully paid and non-assessable.

         We hereby  consent to the  filing of this  opinion as an exhibit to the
Registration  Statement and to the reference made to us under the caption "Legal
Matters" in the prospectus  constituting part of the Registration  Statement. In
giving this consent,  we do not thereby admit that we are within the category of
persons  whose  consent is required  under  Section 7 of the Act,  the rules and
regulations of the Commission promulgated under Section 7 of the Act or Item 509
of Regulation S-B promulgated under the Act.


                                      Very truly yours,

                                      /s/ Jenkens & Gilchrist Parker Chapin LLP
                                      JENKENS & GILCHRIST PARKER CHAPIN LLP