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Employee Compensation Plans - Additional Information (Narrative) (Details) |  |  | 12 Months Ended
--- | --- | --- | ---
Jan. 28, 2021 shares | Jan. 11, 2021 shares | Dec. 31, 2020 USD ($) employee_compensation_plan shares | Dec. 31, 2019 USD ($) | Dec. 31, 2018 USD ($)
Share-based Compensation Arrangement by Share-based Payment Award [Line Items] |  |  |  |  |
Number of Employee Compensation Plans Granted | employee_compensation_plan |  |  | 2 |  |
Maximum annual contribution under Defined Contribution Plan |  |  | $ 19,500 | $ 19,000 | $ 18,500
Employer contribution to Defined Contribution Plan |  |  | 3,500,000 | 2,400,000 | 1,800,000
Deferred bonus amounts |  |  | $ 10,000,000.0 | 9,300,000 | 9,400,000
Vesting period of deferred bonus |  |  | 5 years |  |
Deferred compensation plans cost |  |  | $ 18,100,000 | 19,400,000 | 6,100,000
Class A Stock |  |  |  |  |
Share-based Compensation Arrangement by Share-based Payment Award [Line Items] |  |  |  |  |
Number of shares of Class A Stock available | shares |  |  | 1,279,118 |  |
Restricted Stock | Class A Stock |  |  |  |  |
Share-based Compensation Arrangement by Share-based Payment Award [Line Items] |  |  |  |  |
Aggregate intrinsic value of ESP awards outstanding |  |  | $ 41,800,000 |  |
Compensation expense relating to the share-based awards |  |  | 7,700,000 | 8,100,000 | 6,000,000.0
Unrecognized compensation cost related to unvested share-based compensation |  |  | $ 14,600,000 |  |
Cost is expected to be recognized over a weighted average period |  |  | 1 year 10 months 24 days |  |
Granted, Number of shares | shares |  |  | 471,700 |  |
Share-based Compensation Arrangement by Share-based Payment Award, Equity Instruments Other than Options, Vested in Period | shares |  |  | 623,981 |  |
Restricted Stock | Subsequent Event [Member] | Class A Stock |  |  |  |  |
Share-based Compensation Arrangement by Share-based Payment Award [Line Items] |  |  |  |  |
Granted, Number of shares | shares | 571,940 |  |  |  |
Employee Stock Option |  |  |  |  |
Share-based Compensation Arrangement by Share-based Payment Award [Line Items] |  |  |  |  |
Compensation expense relating to the share-based awards |  |  | $ 25,300 | 26,200 | 26,500
Stock Appreciation Rights (SARs) [Member] |  |  |  |  |
Share-based Compensation Arrangement by Share-based Payment Award [Line Items] |  |  |  |  |
Compensation expense relating to the share-based awards |  |  | $ 8,500,000 | $ 3,700,000 | $ 650,000
Cost is expected to be recognized over a weighted average period |  |  | 3 years 1 month 6 days |  |
Aggregate intrinsic value of OARs outstanding and expected to vest |  |  | $ 17,500,000 |  |
Liability related to the OARs |  |  | 15,400,000 |  |
Total unrecognized compensation cost |  |  | $ 9,500,000 |  |
Stock Appreciation Rights (SARs) [Member] | Subsequent Event [Member] |  |  |  |  |
Share-based Compensation Arrangement by Share-based Payment Award [Line Items] |  |  |  |  |
Vesting period under share based payment |  | 5 years |  |  |
Number Of Stock Appreciation Rights Granted | shares |  | 639,050 |  |  |
Minimum [Member] | Restricted Stock | Subsequent Event [Member] | Class A Stock |  |  |  |  |
Share-based Compensation Arrangement by Share-based Payment Award [Line Items] |  |  |  |  |
Vesting period under share based payment | 3 years |  |  |  |
Maximum [Member] | Restricted Stock | Subsequent Event [Member] | Class A Stock |  |  |  |  |
Share-based Compensation Arrangement by Share-based Payment Award [Line Items] |  |  |  |  |
Vesting period under share based payment | 5 years |  |  |  |
Third Anniversary | Restricted Stock | Subsequent Event [Member] | Class A Stock |  |  |  |  |
Share-based Compensation Arrangement by Share-based Payment Award [Line Items] |  |  |  |  |
Granted, Number of shares | shares | 293,690 |  |  |  |
Fifth Anniversary [Domain] | Restricted Stock | Subsequent Event [Member] | Class A Stock |  |  |  |  |
Share-based Compensation Arrangement by Share-based Payment Award [Line Items] |  |  |  |  |
Share-based Compensation Arrangement by Share-based Payment Award, Equity Instruments Other than Options, Vested in Period | shares | 278,250 |  |  |  |
Oppenheimer Holdings 2014 Incentive Plan (OIP) [Member] | Class A Stock |  |  |  |  |
Share-based Compensation Arrangement by Share-based Payment Award [Line Items] |  |  |  |  |
Term granted for options |  |  | 5 years |  |
Share-based Compensation Arrangement by Share-based Payment Award, Expiration Period |  |  | 6 months |  |
Oppenheimer Holdings 2014 Incentive Plan (OIP) [Member] | Minimum [Member] | Class A Stock |  |  |  |  |
Share-based Compensation Arrangement by Share-based Payment Award [Line Items] |  |  |  |  |
Vesting period under share based payment |  |  | 3 years |  |
Oppenheimer Holdings 2014 Incentive Plan (OIP) [Member] | Maximum [Member] | Class A Stock |  |  |  |  |
Share-based Compensation Arrangement by Share-based Payment Award [Line Items] |  |  |  |  |
Vesting period under share based payment |  |  | 5 years |  |
Oppenheimer Holdings 2014 Incentive Plan (OIP) [Member] | Second Anniversary | Class A Stock |  |  |  |  |
Share-based Compensation Arrangement by Share-based Payment Award [Line Items] |  |  |  |  |
Vesting percentage under share based payment |  |  | 25.00% |  |
Oppenheimer Holdings 2014 Incentive Plan (OIP) [Member] | Third Anniversary | Class A Stock |  |  |  |  |
Share-based Compensation Arrangement by Share-based Payment Award [Line Items] |  |  |  |  |
Vesting percentage under share based payment |  |  | 25.00% |  |
Oppenheimer Holdings 2014 Incentive Plan (OIP) [Member] | Fourth Anniversary | Class A Stock |  |  |  |  |
Share-based Compensation Arrangement by Share-based Payment Award [Line Items] |  |  |  |  |
Vesting percentage under share based payment |  |  | 25.00% |  |
Oppenheimer Holdings 2014 Incentive Plan (OIP) [Member] | Six Months Before Expiration | Class A Stock |  |  |  |  |
Share-based Compensation Arrangement by Share-based Payment Award [Line Items] |  |  |  |  |
Vesting percentage under share based payment |  |  | 25.00% |  |
Oppenheimer Holdings Inc. Stock Appreciation Right Plan | Stock Appreciation Rights [Member] |  |  |  |  |
Share-based Compensation Arrangement by Share-based Payment Award [Line Items] |  |  |  |  |
Vesting period under share based payment |  |  | 5 years |  |
Executive Deferred Compensation Plan and Deferred Incentive Plan |  |  |  |  |
Share-based Compensation Arrangement by Share-based Payment Award [Line Items] |  |  |  |  |
Company's deferred compensation liability |  |  | $ 52,600,000 |  |
CIBC Deferred Compensation Plan |  |  |  |  |
Share-based Compensation Arrangement by Share-based Payment Award [Line Items] |  |  |  |  |
Company's deferred compensation liability |  |  | $ 21,400,000 |  |

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