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                                                                    EXHIBIT 4.21

                          SIXTH SUPPLEMENTAL INDENTURE

     SUPPLEMENTAL INDENTURE (this "Supplemental Indenture"), dated as of October
15, 1998, among Von Hoffmann Press, Inc., a Delaware corporation (the
"Company"), Mid-Missouri Graphics, Inc., a Delaware corporation, One Thousand
Realty & Investment Company, a Delaware Corporation, and Marine Midland Bank, as
trustee under the indenture referred to below (the "Trustee"). Capitalized terms
used herein and not defined herein shall have the meaning ascribed to them in
the Indenture (as defined below).

                               W I T N E S S E T H

     WHEREAS, the Company has heretofore executed and delivered to the Trustee
an indenture (the "Indenture"), dated as of May 22, 1997, providing for the
issuance of an aggregate principal amount of $100,000,000 of 10 3/8% Senior
Subordinated Notes due 2007 (the "Notes");

     WHEREAS, each of Mid-Missouri Graphics, Inc., a Missouri corporation ("MMG
Missouri"), and One thousand Realty & Investment Company, a Missouri corporation
("One thousand Missouri"), is a Guarantor under the Indenture;

     WHEREAS, on October 15, 1998, MMG Missouri merged with and into
Mid-Missouri Graphics, Inc., a Delaware corporation and, prior to such merger, a
wholly-owned subsidiary of MMG Missouri ("MMG Delaware"), with MMG Delaware as
the surviving corporation of such merger;

     WHEREAS, on October 15, 1998, One Thousand Missouri merged with and into
One Thousand Realty & Investment Company, a Delaware corporation and, prior to
such merger, a wholly-owned subsidiary of One Thousand Missouri ("One Thousand
Delaware"), with One Thousand Delaware as the surviving corporation of such
merger;

     WHEREAS, Article 11 of the Indenture provides that under certain
circumstances the Company may or must cause certain of its subsidiaries to
execute and deliver to the Trustee a supplemental indenture pursuant to which
such subsidiaries shall unconditionally guarantee all of the Company's
Obligations under the Notes pursuant to a Notes Guarantee on the terms and
conditions set forth herein; and

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     WHEREAS, pursuant to Section 9.01 of the Indenture, the Trustee is
authorized to execute and deliver this Supplemental Indenture.

     NOW THEREFORE, in consideration of the foregoing and for other good and
valuable consideration, the receipt of which is hereby acknowledged, the
Company, MMG Delaware, One Thousand Delaware and the Trustee mutually covenant
and agree for the equal and ratable benefit of the Holders of the Notes as
follows:

     1.   CAPITALIZED TERMS. Capitalized terms used herein without definition
shall have the meanings assigned to them in the Indenture.

     2.   AGREEMENT TO NOTES GUARANTEE. Each of MMG Delaware and One Thousand
Delaware hereby agrees to assume all of the Obligations of MMG Missouri and One
Thousand Missouri, respectively, as a Guarantor and, as such, agrees, jointly
and severally with all other Guarantors, to guarantee the Company's Obligations
under the Notes and the Indenture on the terms and subject to the conditions set
forth in Article 11 of the Indenture and to be bound by all other applicable
provisions of the Indenture.

     3.   NO RECOURSE AGAINST OTHERS. No past, present or future director,
officer, employee, incorporator, shareholder or agent of any Guarantor, as such,
shall have any liability for any obligations of the Company or any Guarantor
under the Notes, any Notes Guarantees, the Indenture or this Supplemental
Indenture or for any claim based on, in respect of, or by reason of, such
obligations or their creation. Each Holder by accepting a Note waives and
releases all such liability. The waiver and release are part of the
consideration for issuance of the Notes.

     4.   NEW YORK LAW TO GOVERN. THE INTERNAL LAW OF THE STATE OF NEW YORK
SHALL GOVERN AND BE USED TO CONSTRUE THIS SUPPLEMENTAL INDENTURE.

     5.   COUNTERPARTS. The parties may sign any number of copies of this
Supplemental Indenture. Each signed copy shall be an original, but all of them
together represent the same agreement.

     6.   EFFECT OF HEADINGS. The Section headings herein are for convenience
only and shall not affect the construction hereof.

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     7.   THE TRUSTEE. The Trustee shall not be responsible in any manner
whatsoever for or in respect of the validity or sufficiency of this Supplemental
Indenture or for or in respect of the correctness of the recitals of fact
contained herein, all of which recitals are made solely by the Company, MMG
Delaware and One Thousand Delaware.

          IN WITNESS WHEREOF, the parties hereto have caused this Supplemental
Indenture to be duly executed and attested, all as of the date first above
written.

Dated: October 15, 1998              VON HOFFMANN PRESS, INC.

                                     By: /s/ Robert A. Uhlenhop
                                        ----------------------------------------
                                        Robert A. Uhlenhop
                                        President and
                                        Chief Executive
                                        Officer

Dated: October 15, 1998              MID-MISSOURI GRAPHICS, INC.

                                     By: /s/ Robert A. Uhlenhop
                                        ----------------------------------------
                                        Robert A. Uhlenhop
                                        President

Dated: October 15, 1998              ONE THOUSAND REALTY &
                                       INVESTMENT COMPANY

                                     By: /s/ Robert A. Uhlenhop
                                        ----------------------------------------
                                        Robert A. Uhlenhop
                                        President

Dated: October 15, 1998              MARINE MIDLAND BANK,
                                        as Trustee

                                     By: /s/ Marcia Markowski
                                        ----------------------------------------
                                        Name:  Marcia Markowski
                                        Title: Assistant Vice President

                                        3<Page>

                                                                    EXHIBIT 4.22

                         SEVENTH SUPPLEMENTAL INDENTURE

     SUPPLEMENTAL INDENTURE (this "Supplemental Indenture"), dated as of
November 2, 1998, among Von Hoffmann Press, Inc., a Delaware corporation (the
"Company"), Bawden Printing, Inc., a Delaware corporation, and Marine Midland
Bank, as trustee under the indenture referred to below (the "Trustee").
Capitalized terms used herein and not defined herein shall have the meaning
ascribed to them in the Indenture (as defined below).

                               W I T N E S S E T H

     WHEREAS, the Company has heretofore executed and delivered to the Trustee
an indenture (the "Indenture"), dated as of May 22, 1997, providing for the
issuance of an aggregate principal amount of $100,000,000 of 10 3/8% Senior
Subordinated Notes due 2007 (the "Notes");

     WHEREAS, each of The Bawden Corporation, an Iowa corporation ("BC"), and
Bawden Printing, Inc., an Iowa corporation ("BP Iowa"), executed and delivered
to the Trustee a Supplemental Indenture, dated as of January 16, 1998, pursuant
to which each of BC and BP Iowa became Guarantors under the Indenture;

     WHEREAS, as permitted by Section 11.03(a) of the Indenture, on August 3,
1998, BP Iowa was merged with and into BC, and, following consummation of such
merger, BC, as the surviving corporation, changed its name to "Bawden Printing,
Inc." (BC, as the re-named surviving corporation of such merger, is hereinafter
referred to as "New BP Iowa");

     WHEREAS, on November 2, 1998, New BP Iowa merged with and into Bawden
Printing, Inc., a Delaware corporation and, prior to such merger, a wholly-owned
subsidiary of New BP Iowa ("BP Delaware"), with BP Delaware as the surviving
corporation of such merger;

     WHEREAS, Article 11 of the Indenture provides that under certain
circumstances the Company may or must cause certain of its subsidiaries to
execute and deliver to the Trustee a supplemental indenture pursuant to which
such subsidiaries shall unconditionally guarantee all of the

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Company's Obligations under the Notes pursuant to a Notes Guarantee on the terms
and conditions set forth herein; and

     WHEREAS, pursuant to Section 9.01 of the Indenture, the Trustee is
authorized to execute and deliver this Supplemental Indenture.

     NOW THEREFORE, in consideration of the foregoing and for other good and
valuable consideration, the receipt of which is hereby acknowledged, the
Company, BP Delaware, and the Trustee mutually covenant and agree for the equal
and ratable benefit of the Holders of the Notes as follows:

     1.   CAPITALIZED TERMS. Capitalized terms used herein without definition
shall have the meanings assigned to them in the Indenture.

     2.   AGREEMENT TO NOTES GUARANTEE. BP Delaware hereby agrees to assume all
of the Obligations of New BP Iowa as a Guarantor and, as such, agrees, jointly
and severally with all other Guarantors, to guarantee the Company's Obligations
under the Notes and the Indenture on the terms and subject to the conditions set
forth in Article 11 of the Indenture and to be bound by all other applicable
provisions of the Indenture.

     3.   NO RECOURSE AGAINST OTHERS. No past, present or future director,
officer, employee, incorporator, shareholder or agent of any Guarantor, as such,
shall have any liability for any obligations of the Company or any Guarantor
under the Notes, any Notes Guarantees, the Indenture or this Supplemental
Indenture or for any claim based on, in respect of, or by reason of, such
obligations or their creation. Each Holder by accepting a Note waives and
releases all such liability. The waiver and release are part of the
consideration for issuance of the Notes.

     4.   NEW YORK LAW TO GOVERN. THE INTERNAL LAW OF THE STATE OF NEW YORK
SHALL GOVERN AND BE USED TO CONSTRUE THIS SUPPLEMENTAL INDENTURE.

     5.   COUNTERPARTS. The parties may sign any number of copies of this
Supplemental Indenture. Each signed copy shall be an original, but all of them
together represent the same agreement.

                                        2
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     6.   EFFECT OF HEADINGS. The Section headings herein are for convenience
only and shall not affect the construction hereof.

     7.   THE TRUSTEE. The Trustee shall not be responsible in any manner
whatsoever for or in respect of the validity or sufficiency of this Supplemental
Indenture or for or in respect of the correctness of the recitals of fact
contained herein, all of which recitals are made solely by the Company and BP
Delaware.

          IN WITNESS WHEREOF, the parties hereto have caused this Supplemental
Indenture to be duly executed and attested, all as of the date first above
written.

Dated: November 2, 1998              VON HOFFMANN PRESS, INC.

                                     By: /s/ Robert A. Uhlenhop
                                        ----------------------------------------
                                        Robert A. Uhlenhop
                                        President and
                                        Chief Executive
                                        Officer

Dated: November 2, 1998              BAWDEN PRINTING, INC.

                                     By: /s/ Robert A. Uhlenhop
                                        ----------------------------------------
                                        Robert A. Uhlenhop
                                        Chief Executive Officer

Dated: November 2, 1998              MARINE MIDLAND BANK,
                                        as Trustee

                                     By: /s/ Marcia Markowski
                                        ----------------------------------------
                                        Name:  Marcia Markowski
                                        Title: Assistant Vice President

                                        3

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