The Power of Variable Income Annuity Payments

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The Power of Variable Income Annuity Payments What s Driving Your Retirement Income? insure invest retire Retirement Income

MassMutual RetireEase Select SM MassMutual RetireEase Select is a single premium immediate variable annuity that combines income guarantees with income growth potential. The contract can help supplement your retirement income with guaranteed payments for life or for a specific period of time. Guarantees are based on the claims-paying ability of the issuing company. Key Features Guaranteed lifetime income life annuity payments offer income that can t be outlived. Professional investment management professionally managed variable investment choices are available, plus asset allocation models. Income growth potential if your investment choices perform well, your income has the potential to grow over time. Tax benefits for contracts funded with after-tax dollars, a portion of each annuity payment will be excluded from tax, until the amount of the investment has been recovered. Access to cash withdrawals if you choose a payment method that includes a period certain, access is available to you during retirement or for your beneficiary upon your death. Optional Features MassMutual Payment Protector SM provides an income floor on variable payments. Available for an additional charge of 0.50%. MassMutual Budget Protector SM provides level payments over a 12-month period. MassMutual Inflation Protector SM you can elect to automatically increase fixed income payments on an annual basis by 1%, 2%, 3% or 4%. MassMutual RetireEase Select s key features make it uniquely suited to help drive your retirement income in a direction that meets your needs. The following pages will help you better understand why guaranteed income and growth potential can be so important in retirement. NOT A BANK OR CREDIT UNION DEPOSIT OR OBLIGATION NOT FDIC OR NCUA-INSURED NOT INSURED BY ANY FEDERAL GOVERNMENT AGENCY NOT GUARANTEED BY ANY BANK OR CREDIT UNION MAY GO DOWN IN VALUE This This presentation must must be preceded be preceded or accompanied or accompanied by the by current the current prospectuses for MassMutual RetireEase Select single premium immedi- immediate variable variable annuity annuity and its and underlying its underlying investment choices. choices. Before purchasing purchasing a variable a variable annuity contract, annuity contract, investors investors should carefully should carefully consider Before consider the investment the investment objectives, objectives, risks, charges risks, charges and expenses and expenses of the of variable the variable annuity annuity contract contract and its and underlying its underlying investment investment choices. choices. Please Please read the read prospectus the prospectuses carefully carefully before investing before investing or sending or money. sending money.

The Power of Variable In Why add a variable income annuity to your retirement plan? Consider this MassMutual RetireEase Select historical illustration using the MML Oppenheimer/Bernstein Equity Sub- Account which has over 30-years of investment performance history. Note not only the growth potential of this equity-based investment choice, but how income will fluctuate with investment performance. MassMutual RetireEase Select Historical Illustration Time Period: 12/31/1977 through 12/31/2007 MML Oppenheimer/Bernstein Equity one of more than 40 investment choices Assumptions: Male & Female both age 65 Joint & Survivor with 10-year Period Certain Payment Method Assumed Investment Rate (AIR): 3% Payment Frequency: monthly 100,000 initial investment on 12/31/1977 Initial Estimated Monthly Payment: 456 Inflation: Growth of 456 adjusted monthly using the Consumer Price Index (CPI) 100,000 cost basis recovered by 2003 Glossary of Terms Joint & Survivor with 10-year Period Certain Payments are guaranteed for a minimum of 10 years. However, if the annuitants live longer than 10 years, payments will continue for as long as either annuitant is alive. Guarantees are based on the claims-paying ability of the issuing company. Assumed Investment Rate (AIR) A benchmark used to determine variable income annuity payment amounts. It is not a guaranteed rate of return, but is an investment rate used to set the initial income payment and determine if variable payments will increase or decrease in the future. Initial Estimated Monthly Payment Considered the starting point for income payments. It s based on the annuitant(s) age, gender, annuity payment method, payment frequency and the single premium amount. Additional optional features elected may also affect it. Standardized Total Returns as of 6/30/08 These are SEC required returns since the date the fund was first made available to the separate account. The performance numbers below assume a single 1,000 payment made at the beginning of the period, the election of the Payment Protector feature and full redemption at the end with a deduction for: Contingent Deferred Sales Charges (CDSC) Only applies to full or partial withdrawals from annuity payment methods with a period certain. Contract Year: 1 2 3 4 5 6 7 8 9 10+ 8% 8% 7% 6% 5% 4% 3% 2% 1% 0% Total fund operating expenses and total separate account expenses of 1.75% These returns do not reflect premium taxes, if any. Their inclusion would reduce the returns shown. Please note that the amount of the CDSC depends on the amount you withdraw and the length of time between when we issue your contract and when you make a withdrawal. Sub-Account (date fund was made available to the separate account) MML Oppenheimer/Bernstein Equity (4/30/99) 1-Year 5-Year Since Available in Separate Account 25.99% 5.23% 1.26% Performance shown is historical and does not guarantee future results. Current performance may be lower or higher than that illustrated. Variable income annuity payments will fluctuate and may be higher or lower than the initial estimated payment amount. It s possible to receive back less income than the original investment amount. Monthly performance updates are posted on our website at www.massmutual.com and are available by calling the Annuity Service Center Monday through Friday 8 a.m. 8 p.m. ET at (800) 272-2216 (option 2). Cost of items (next page) sources House: flashback.com, 2007, Gallon of Gas: flashback.com, U.S. Dept. of Energy, 2007, Dozen Eggs: flashback.com, U.S. Bureau of Labor Statistics, 2007 2007 Cost of items House: www.census.gov, Gallon of Gas: Energy Information Administration, U.S. Government Statistics, release date 9/2/2008, Dozen Eggs: American Farm Bureau, www.fb.org

ome Annuity Payments 70,000 60,000 50,000 40,000 30,000 20,000 10,000 3,978 0 Calendar Year Returns Cumulative Income: 862,190 Sum of 12 Monthly Payments Cost Basis Inflation Camp David Peace Treaty Iranian Hostage Crisis Begins U.S. Boycotts Moscow Olympics Pope and Reagan are Shot Recession Starts U.S. Invades Grenada USSR Withdraws from LA Olympics U.S. Budget Balancing Bill Enacted Iran-Contra Affair Begins 14,97 10,048 10,292 12,008 7,490 7,627 5,285 5,678 6,491 1978 1979 1980 1981 1982 1983 1984 1985 198 2.43% 18.03% 26.04% 5.34% 24.11% 21.30% 4.11% 28.87% 18.65 Cost of items: house gallon of gas dozen eggs 62,500 71,800 76,400 83,000 83,900 89,800 97,600 100,800 111,9 0.63 0.86 1.25 1.38 1.30 1.24 1.21 1.20 0.9 0.82 0.85 0.84 0.90 0.87 0.89 1.00 0.80 0.8 *Dow Jones Industrial Average (DJIA) a price-weighted average of 30 actively traded blue-chip stocks, primarily industrials

Stock Market Crash Soviets Withdraw from Afghanistan Berlin Wall Comes Down Recession Starts Gulf War I Begins 21,888 Los Angeles Riots 24,251 World Trade Center Bombing 26,281 Whitewater Scandal Begins 27,516 Oklahoma City Federal Building Bombing 31,416 Unabomber Arrested 37,620 DJIA Closes Over 7,000* 46,772 18,715 18,885 9 16,955 16,390 6 1987 1988 1989 1990 1991 1992 1993 1994 1995 1996 1997 % 0.84% 15.23% 21.52% 0.33% 26.10% 10.55% 11.72% 2.82% 31.17% 21.37% 34.12% 00 127,200 138,300 148,800 149,800 147,200 144,100 147,700 154,500 158,700 166,400 176,200 3 0.95 1.08 1.12 1.16 1.14 1.13 1.11 1.11 1.15 1.23 1.23 7 0.78 0.79 1.00 1.01 0.99 0.86 0.91 0.86 0.92 1.11 1.06. A frequently used measure of U.S. stock market performance.

Financial Crisis in South East Asia 56,226 DJIA Hits 11,000* 60,268 Internet Bubble Bursts 54,420 9/11 Terrorist Attack Corporate Accounting Scandals Gulf War II Begins Tsunami Hits South Asia 44,291 Hurricane Katrina 47,176 DJIA Hits 12,000* 50,024 Crude Oil Price Soars 56,203 39,899 38,015 38,015 1998 1999 2000 2001 2002 2003 2004 2005 2006 2007 18.27% 5.01% 1.63% 15.78% 20.55% 25.91% 14.26% 1.85% 16.54% 2.71% 181,900 195,800 207,000 213,200 228,700 246,300 274,500 297,000 305,900 286,275 1.06 1.17 1.46 1.38 1.29 1.50 1.81 2.24 2.53 2.79 1.04 0.96 0.91 0.93 1.03 1.24 1.34 1.22 1.31 1.61

Inflation A Threat to Purchasing Power Inflation is one of several risks investors will face in retirement. Inflation erodes purchasing power over time, because as prices rise, a dollar buys less. For example: 1981: 20 2008: 42 In 1981, 1 could have bought 5 stamps, but in 2008 the same dollar could only buy two stamps. 1 In the future, people may spend 20 or even 30 years in retirement. That means over time your income needs to maintain a rising income pattern in order to preserve your purchasing power and to maintain your standard of living. Income Pattern to Maintain Standard of Living 400,000 300,000 200,000 100,000 0 60 65 70 75 80 85 90 95 100 The chart above assumes a starting income of 70,000 a year at age 60 and income increasing by 4% per year to keep pace with inflation. The Value of Equities Over the Long-term The true power of variable income annuity payments comes from an individual s ability to invest in equity-based investment choices. Historically, equities (stocks) have outpaced inflation as well as other asset classes such as bonds and cash over the long-term. For that reason, investing in equities offers the growth potential for a retirement that could span many years. 30-Year Average Annual Returns Stocks 12.9% Bonds 9.3% Cash 6.1% Inflation 4.1% Data Source: S&P Micro Pal Returns as of 12/31/07 Stocks: Represented by the S&P 500 Index which is a list of securities frequently used as a measure of U.S. stock market performance. Bonds: Represented by the Lehman Long-term Credit Index which includes U.S. Treasuries (with remaining maturities of more than one year), Government-Related issues and USD-denominated Corporate investment-grade, fixed-rate, taxable securities sold by industrial, utility and financial issuers. It includes publicly issued U.S. corporate and foreign debentures and secured notes that meet specified maturity, liquidity, and quality requirements. Cash: Represented by the Treasury Bills Index which measures short-term debt obligations of the U.S. government with a maturity of less than three months. Inflation: Represented by the Consumer Price Index. Indices are unmanaged and do not represent the performance of any MassMutual product or specific underlying fund. Indices are not available for direct investment. Past performance is not indicative of future results. 1 U.S. Postal Service, 2008 Choosing the right vehicle is never easy. But MassMutual RetireEase Select is an investment vehicle specifically designed to help drive retirement income.

MassMutual RetireEase Select [Policy Form # SPIVA05 countrywide, in North Carolina, the form number is SPIVA05(NC)] is an immediate variable annuity contract issued by Massachusetts Mutual Life Insurance Company, 1295 State Street, Springfield, MA 01111-0001. Principal Underwriter: MML Distributors, LLC, 1295 State Street, Springfield, MA 01111-0001. Wholly owned subsidiary of Massachusetts Mutual Life Insurance Company. Massachusetts Mutual Life Insurance Company and affiliates, Springfield, MA 01111-0001 www.massmutual.com 2008 Massachusetts Mutual Life Insurance Company. All rights reserved. MassMutual Financial Group is a marketing name for Massachusetts Mutual Life Insurance Company (MassMutual) and its affiliated companies and sales representatives. AN2315 908 RI01404 910