On November 3, 1905, a new enterprise, Southeastern Life Insurance Company, came into existence in Spartanburg, South Carolina. Fourteen years later on October 13, W. Frank Hipp, a former agent of that company, established a new company, Liberty Life Insurance Company, in Greenville, South Carolina. In 1933, Hipp became president of both companies, which continued to operate separately. However, on January 1, 1942, the insurance companies were consolidated under the name of Liberty Life Insurance Company, with Hipp as president. W. Frank Hipp died on January 3, 1943. On January 29, The Board of Directors voted Francis M. Hipp to succeed his father as president of Liberty Life and made his brother, Herman N. Hipp, the company's vice president and director.

Liberty Life Insurance Company became one of the subsidiaries of a new holding company, The Liberty Corporation, on December 1, 1967. The other subsidiaries included Cosmos Broadcasting Corporation, Surety Investment Company, and Liberty Properties, Inc. In addition, a new subsidiary, Liberty Investors Benefit Insurance (LIBCO), was organized for the purpose of writing individual and group variable annuity contracts. Thanks to an exceptional sales effort, Liberty Life ended 1968 with over $2.5 billion of life insurance in force. Also during that year, a leading management consulting firm examined the structure of the insurance company. As a result of that study, Liberty Life made administrative changes that resulted in the naming of six new Vice Presidents in the functional areas of Insurance Operations, Investments, and Administration. In 1969 W. Hayne Hipp, son of Francis Hipp, became assistant vice president of Liberty Life. The insurance company introduced two completely new lines of policies, "The Sentinel Plan" and the "Thrift Series". Created for young family purchasers, Sentinel offered a minimum of $10,000 insurance coverage with an accompanying fast accumulation of cash values resulting in high savings at retirement age. The Thrift Series was a unique variation of typical weekly premium and monthly debit ordinary policies, which included many of the beneficial features of modern, regular ordinary policies such as modes of premium payment adjustable to changing income levels. These new products helped to improve and expand the ordinary and group departments, and by the end of the 1960s, Liberty Life was licensed in 24 states and Puerto Rico.

The insurance company saw a number of changes in the 1970s. The traditional industrial insurance had faded out by the beginning of the decade, but the debit system and the weekly collection option continued to exist, and customers now purchased a variation on the typical ordinary life contract. In 1970 the Combination Department experienced significant success in selling a new cancer expense policy and the Group Department introduced a new program of group life, disability income and comprehensive medical care protection primarily for groups of 10 to 49 persons. The Ordinary Department formed a securities, broker-dealer operation to sell a combination of insurance and mutual funds in 1971. The personnel of the insurance company's Securities Department were assigned to a new, wholly owned investment-counseling subsidiary of the holding company, Liberty Investment Management Corporation (LIMCO). In 1973 Liberty Life arrived at $4 billion of insurance in force. By 1975 Liberty Life was in the top five per cent of the insurance companies in the United States in terms of insurance in force. During that year the popular Thrift line of debit insurance was revised to provide increased amounts of protection to match rising incomes among working people. Also, the Combination agents began marketing a new Special Monthly Custom Series, which combined the personal contact elements of home service policies with the increased protection of Ordinary plans. Both of these lines helped the insurance company during the economic troubles of the mid-1970s.

By this time Liberty Life Insurance Company faced more competition in the insurance market from the increasing number of out-of-state insurance companies chartered to operate in South Carolina. In addition, there was growing criticism of the insurance industry from a variety of sources, including the Federal Trade Commission, the United States Senate Judiciary Committee, the South Carolina Legislature Audit Council, and the news media. In an effort to maintain a favorable corporate image, the company launched a major public relations program, "Have a Good Life", in 1977. This campaign, which ran through 1981, encouraged people to take charge of their lives and improve their health.

On March 1, 1977 Herman N. Hipp became president and chief executive officer of The Liberty Corporation. He succeeded his brother, Francis M. Hipp, who retired from that office but continued to serve as chairman of the board of directors and the executive committee. Harris P. Gravely became president and chief executive officer of Liberty Life Insurance Company, and Hayne Hipp was promoted to be its executive vice president. At the beginning of October 1977, Liberty Life purchased United Fidelity Life Insurance Company of Dallas, Texas. On January 1, 1978 Liberty Properties, Inc. was merged into Liberty Life and became a division of its Investment Department. And in 1978 Hayne Hipp was elected as Vice Chairman and Chief Executive Officer of The Liberty Corporation and Chairman of Liberty Life.

In 1978 a marketing study led to the establishment of 75 new projects to be completed by 1980 to meet changing market conditions. One of the new products that came out in 1981 was the "ANSWER", a universal life policy which credited current interest rates and allowed for varying insurance needs of policyholders through flexibility in premium payments and the amount of coverage. With this flexibility, the policyholder rarely needed to switch or add policies, therefore avoiding additional first-year acquisition charges.

In 1982 R. Glen Hilliard and Richard W. Campanaro were promoted to President and Vice President of Liberty Life. Proving to be unprofitable, United Fidelity Life Insurance Company was sold that same year. In 1984 Liberty Life reached $10 billion insurance in force, and in the next year, when the company celebrated its 80th Anniversary, it topped at $11 billion insurance in force. At the end of 1986, Liberty Life enlarged and strengthened its Career Agency Marketing division by acquiring Southern Life Insurance Company in Greensboro, North Carolina. In 1987 the insurance company sold its group insurance operations, and then enhanced its Specialized Marketing Division with the purchase of Triad Life Insurance Company of Winston-Salem, North Carolina in 1989. By the end of the 1980s, Liberty Life Insurance Company, with $15.7 billion of life insurance in force, was among the largest 5% of stock life insurance companies in America, and was licensed in 46 states and the District of Columbia.

During the early 1990s Liberty Life Insurance Company purchased several pre-need and home services companies which were later sold. In February 1999 The Liberty Corporation announced that it was considering a variety of restructuring alternatives that would actively support the business objectives of its operating subsidiaries and enhance value for shareholders. In May of that year, The Corporation hired Goldman Sachs to look at possible separation of its businesses or other restructuring. On March 20, 2000 Liberty Life Insurance Company announced that it would expand its insurance administration services in Canada through an exclusive agreement with CAS Accounting for Insurance Inc. Soon after this came the announcement, on June 19, 2000, that The Liberty Corporation was selling its insurance operations (Liberty Life Insurance and Liberty Insurance Services Corporation) and its real estate holdings (including the headquarters building in Greenville, South Carolina) to the Royal Bank of Canada for $650 million. In addition, The Corporation announced its plan to merge Cosmos Broadcasting with Jackson, Mississippi based Civic Communications, under which The Corporation would pay Civic $204 million in cash. On November 1, 2000, the sales agreement between The Liberty Corporation and the Royal Bank of Canada was completed, and the Hipp family no longer owned Liberty Life Insurance Company.